CN116606186A - Aromatic nitro compound and preparation method thereof - Google Patents
Aromatic nitro compound and preparation method thereof Download PDFInfo
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- CN116606186A CN116606186A CN202310578387.8A CN202310578387A CN116606186A CN 116606186 A CN116606186 A CN 116606186A CN 202310578387 A CN202310578387 A CN 202310578387A CN 116606186 A CN116606186 A CN 116606186A
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- -1 Aromatic nitro compound Chemical class 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 229910002651 NO3 Inorganic materials 0.000 claims abstract description 10
- 239000000047 product Substances 0.000 claims abstract description 10
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 7
- 238000001704 evaporation Methods 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 4
- LLNAMUJRIZIXHF-CLFYSBASSA-N (z)-2-methyl-3-phenylprop-2-en-1-ol Chemical compound OCC(/C)=C\C1=CC=CC=C1 LLNAMUJRIZIXHF-CLFYSBASSA-N 0.000 claims description 3
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 235000010333 potassium nitrate Nutrition 0.000 claims description 2
- 239000004323 potassium nitrate Substances 0.000 claims description 2
- 235000010344 sodium nitrate Nutrition 0.000 claims description 2
- 239000004317 sodium nitrate Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 150000001492 aromatic hydrocarbon derivatives Chemical class 0.000 claims 3
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 230000035484 reaction time Effects 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 5
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 3
- OWPIFQXNMLDXKW-UHFFFAOYSA-N tert-butyl indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1 OWPIFQXNMLDXKW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BLZKSRBAQDZAIX-UHFFFAOYSA-N 2-methyl-1-benzothiophene Chemical compound C1=CC=C2SC(C)=CC2=C1 BLZKSRBAQDZAIX-UHFFFAOYSA-N 0.000 description 2
- CXPMUBPMTBGZQX-UHFFFAOYSA-N 2-methyl-3-nitro-1-benzothiophene Chemical compound C1=CC=C2C([N+]([O-])=O)=C(C)SC2=C1 CXPMUBPMTBGZQX-UHFFFAOYSA-N 0.000 description 2
- LSIKFJXEYJIZNB-UHFFFAOYSA-N 9-Nitroanthracene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(C=CC=C3)C3=CC2=C1 LSIKFJXEYJIZNB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
- 229960002074 flutamide Drugs 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/02—Formation or introduction of functional groups containing nitrogen of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of an aromatic nitro compound, which comprises the following steps: adding solvent and nitrate into N-Boc-indole as raw materials, dropwise adding anhydride at a certain reaction temperature to react for a period of time, extracting, drying, filtering, evaporating the solvent under reduced pressure to obtain crude aromatic nitro compound, and further purifying the crude aromatic nitro compound to obtain a pure product; the invention takes the electron-rich aromatic hydrocarbon as the raw material, can obtain the aromatic nitro compound under the condition of approaching room temperature without nitric acid, has few byproducts and high yield, can realize commercial large-scale preparation and production, and meets the current continuously-growing market demand.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to an aromatic nitro compound and a preparation method thereof.
Background
Aromatic nitro compound is a very important multipurpose chemical raw material and is a multipurpose intermediate for synthesis. Many aromatic nitro compounds can also be used as medicaments per se, for example nifedipine has antihypertensive effect and flutamide is used for treating prostate cancer. Many aromatic nitro compounds are widely used as chemical raw materials and organic synthetic reagents in the industries of medicine, dyes, fragrances, explosives and the like. In recent years, the aromatic nitro compound has wider application, and plays an important role in the aspects of nano fluorescent materials, high molecular antibacterial materials, metal organic frameworks, drug toxicity research and the like.
At present, although many documents report on the synthesis of aromatic nitro compounds, some disadvantages still exist, such as nitric acid is needed in the synthesis process: the reaction yield is too low, and the later purification is difficult; the reaction conditions are severe, and explosion risks exist; the reaction temperature is minus 78 ℃, and the energy consumption is high; and strong acid corrodes the equipment; mass production is limited and safety risks are high.
Disclosure of Invention
The invention aims to provide an aromatic nitro compound and a preparation method thereof, which take electron-rich aromatic hydrocarbon as a starting material to prepare a target product. The aromatic nitro compound is prepared efficiently and safely through one-step electrophilic nitration. More importantly, the invention develops a synthesis method for preparing the aromatic nitro compound under the condition of approaching room temperature without nitric acid, and the reaction mechanism is as follows:
the inventor has found through research that: the metathesis of a nitrate salt (e.g., tetramethyl ammonium nitrate described above) with an anhydride (e.g., trifluoroacetic anhydride described above) to form a nitrate ester (e.g., trifluoroacetic nitrate (a) described above), a being a strong electrophile capable of forming a quaternary cyclic intermediate B, B with an electron-rich aromatic hydrocarbon for further conversion to an aromatic nitro compound. Makes up the defects and shortages of the current synthetic method for preparing the aromatic nitro compound. The synthesis process has the advantages of simple equipment, easy operation, environmental friendliness, low cost and high yield, and can realize commercial large-scale preparation and production so as to meet the current continuously-growing market demands.
The embodiment of the invention is realized by the following technical scheme:
a process for the preparation of an aromatic nitro compound comprising the steps of:
the method comprises the steps of taking electron-rich aromatic hydrocarbon as a raw material, adding a solvent and nitrate, dripping anhydride under stirring at the temperature of minus 20-25 ℃, reacting for 1-8 hours at the temperature of minus 20-25 ℃, extracting, drying, filtering, decompressing and evaporating the solvent to obtain an aromatic nitro compound crude product, and further purifying the crude product to obtain a pure product.
The technical scheme of the embodiment of the invention has at least the following advantages and beneficial effects:
the method for synthesizing the aromatic nitro compound can obtain the aromatic nitro compound with high yield under the condition of approaching room temperature without nitric acid, has few byproducts, uses low-price and easily-obtained raw materials, has mild reaction conditions, is environment-friendly, has low cost and high yield, can realize commercial large-scale preparation and production, and meets the current continuously-growing market demands.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The following describes a preparation method of an aromatic nitro compound provided in the embodiment of the invention.
A method for preparing an aromatic nitro compound, comprising the steps of:
the method comprises the steps of taking electron-rich aromatic hydrocarbon as a raw material, adding a solvent and nitrate, dripping anhydride under stirring at the temperature of minus 20-25 ℃, reacting for 1-8 hours at the temperature of minus 20-25 ℃, extracting, drying, filtering, decompressing and evaporating the solvent to obtain an aromatic nitro compound crude product, and further purifying the crude product to obtain a pure product.
Further, the molar ratio of the nitrate to the N-Boc-indole is 1:1-4:1.
Further, the molar ratio of the N-Boc-indole to the anhydride is 1:1-1:8.
Further, the nitrate is selected from one or more of salt potassium nitrate, sodium nitrate, tetramethyl ammonium nitrate or tetrabutyl ammonium nitrate.
Further, the solvent is preferably one or more of esters and nitriles; such as tetrahydrofuran, 1, 4-dioxane, acetonitrile, dichloromethane, 1, 2-dichloroethane, ethyl acetate or xylene.
Further, the anhydride is selected from one or more of trifluoroacetic anhydride, trifluoromethanesulfonic anhydride or acetic anhydride.
Further, the extraction solvent is one or more of ethyl acetate, dichloromethane or 1, 2-dichloroethane during extraction.
Further, the said method may use one or several of column chromatography separation and recrystallization.
Several specific methods for preparing aromatic nitro compounds are provided below.
Example 1
Preparation of 1-nitronaphthalene: 12.7kg of naphthalene, 15kg of tetramethyl ammonium nitrate and 200L of acetonitrile are sequentially added into a reaction kettle, the temperature is reduced to 15 ℃, 18kg of trifluoroacetic anhydride is added for reaction for 5 hours, then water quenching reaction is added, ethyl acetate is used for extraction, anhydrous magnesium sulfate is used for drying, filtration and reduced pressure evaporation are carried out to remove the solvent, thus obtaining 16.4kg of pure product, and the yield is 95 percent.
1 H NMR(400MHz,CDCl 3 ):δ8.59(dd,J＝8.7,1.0Hz,1H),8.26(dd,J＝7.7,1.2Hz,1H),8.14(d,J＝8.3Hz,1H),7.98(d,J＝8.2Hz,1H),7.74(ddd,J＝8.6,6.9,1.4Hz,1H),7.65(ddd,J＝8.1,6.8,1.2Hz,1H),7.57(t,J＝7.9Hz,1H).
13 C NMR(101MHz,CDCl 3 ):δ146.6,134.7,134.3,129.5,128.6,127.4,125.1,124.2,124.1,123.1.
HRMS(ESI-TOF)m/z:[M+H]+Calcd for C 10 H 8 NO 2 174.0555；found 174.0551.
Example 2
Preparation of 9-nitroanthracene: sequentially adding 17.7kg of anthracene, 35kg of tetrabutylammonium nitrate and 200L of acetonitrile into a reaction kettle, cooling to 5 ℃, adding 26kg of trifluoroacetic anhydride, reacting for 2 hours, then adding water for quenching reaction, extracting with ethyl acetate, drying with anhydrous magnesium sulfate, filtering, evaporating under reduced pressure to remove a solvent to obtain a crude 9-nitroanthracene product, adding absolute ethyl alcohol into the crude product, heating until the crude product is completely dissolved, cooling and crystallizing; drying under reduced pressure to obtain 19.6kg of pure product with 88% yield.
1 H NMR(600MHz,CDCl 3 ):δ8.60(s,1H),8.06(d,J＝8.5Hz,2H),7.94(dd,J＝8.9,1.1Hz,2H),7.68-7.62(m,2H),7.56(td,J＝7.6,7.1,1.6Hz,2H).
13 C NMR(151MHz,CDCl 3 ):δ144.2,130.8,130.8,130.4,128.9,128.4,126.2,126.2,122.7,122.6,121.4,121.4.
HRMS(ESI-TOF)m/z:[M+H]+Calcd for C 14 H 10 NO 2 224.0712；found 224.0708.
Example 3
Preparation of 2-methyl-3-nitrobenzothiophene: 14.7g of 2-methylbenzothiophene and 15g of tetramethyl ammonium nitrate are sequentially added into a reaction kettle, 220mL of ethyl acetate is cooled to 20 ℃, 27g of trifluoroacetic anhydride is added for reaction for 6 hours, then water quenching reaction is added, ethyl acetate extraction, anhydrous magnesium sulfate drying and filtration are carried out, the solvent is removed by evaporation under reduced pressure, and then 17.1g of pure product is obtained from crude 2-methyl-3-nitrobenzothiophene and the crude product is purified by column chromatography, and the yield is 89%.
1 H NMR(600MHz,CDCl 3 ):δ8.45(dd,J＝9.2,4.8Hz,1H),7.78-7.72(m,1H),7.57-7.50(m,1H),7.43(td,J＝7.1,6.6,1.6Hz,1H),2.92(s,3H).
13 C NMR(151MHz,CDCl 3 ):δ149.3,138.6,134.4,132.1,126.7,125.9,123.6,121.9,17.2.
HRMS(ESI-TOF)m/z:[M+Na]+Calcd for C 9 H 7 NO 2 NaS 216.0095；found 216.0090.
In summary, the method for synthesizing the aromatic nitro compound does not use nitric acid, can obtain the aromatic nitro compound with high yield under the condition of approaching room temperature, has few byproducts, uses low-cost and easily-obtained raw materials, has mild reaction conditions, is environment-friendly, has low cost and high yield, and can realize commercial large-scale preparation and production so as to meet the current continuously-growing market demands.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. A method for preparing an aromatic nitro compound, comprising the steps of:
the method comprises the steps of taking an electron-rich aromatic hydrocarbon derivative as a raw material, adding a solvent and nitrate, dripping anhydride at a certain reaction temperature for reacting for a period of time, extracting, drying, filtering, decompressing and evaporating the solvent to obtain an aromatic nitro compound crude product, and further purifying the crude product to obtain a pure product.
2. The method for producing an aromatic nitro compound according to claim 1, wherein the molar ratio of the nitrate to the electron-rich aromatic hydrocarbon derivative is 1:1 to 4:1.
3. The method for producing an aromatic nitro compound according to claim 1, wherein the molar ratio of the electron-rich aromatic hydrocarbon derivative to the acid anhydride is 1:1 to 1:8.
4. The method for producing an aromatic nitro compound according to claim 1, wherein the reaction temperature is-20 to 25 ℃ and the reaction time is 1 to 8 hours.
5. The method for producing an aromatic nitro compound according to claim 1, wherein the nitrate is one or more selected from the group consisting of potassium nitrate, sodium nitrate, tetramethyl ammonium nitrate and tetrabutyl ammonium nitrate.
6. The method for producing an aromatic nitro compound according to claim 1, wherein the solvent is one or more selected from tetrahydrofuran, 1, 4-dioxane, acetonitrile, methylene chloride, 1, 2-dichloroethane, ethyl acetate and xylene.
7. The method for producing an aromatic nitro compound according to claim 1, wherein the acid anhydride is one or more selected from the group consisting of trifluoroacetic anhydride, trifluoromethanesulfonic anhydride and acetic anhydride.
8. The method for preparing aromatic nitro compound according to claim 1, wherein the extraction solvent is one or more of ethyl acetate, dichloromethane or 1, 2-dichloroethane.
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