CN101381302B - 2-bromomethyl-6-methyl benzoyl chloride/bromium and preparation method thereof - Google Patents
2-bromomethyl-6-methyl benzoyl chloride/bromium and preparation method thereof Download PDFInfo
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- CN101381302B CN101381302B CN 200710045693 CN200710045693A CN101381302B CN 101381302 B CN101381302 B CN 101381302B CN 200710045693 CN200710045693 CN 200710045693 CN 200710045693 A CN200710045693 A CN 200710045693A CN 101381302 B CN101381302 B CN 101381302B
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- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 33
- 150000001648 bromium Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title abstract description 8
- GXTCTJROMUDTJV-UHFFFAOYSA-N 2-(bromomethyl)-6-methylbenzoyl chloride Chemical compound BrCC1=C(C(=O)Cl)C(=CC=C1)C GXTCTJROMUDTJV-UHFFFAOYSA-N 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 8
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 8
- 229940125782 compound 2 Drugs 0.000 claims description 8
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 8
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 6
- -1 compound 2-bromomethyl-6-methyl benzoyl chloride Chemical class 0.000 claims description 5
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 5
- YSSRRWLNPLLWPH-UHFFFAOYSA-N BrN(C(=O)N)C(CO)=O Chemical compound BrN(C(=O)N)C(CO)=O YSSRRWLNPLLWPH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- DORVKAJYRZXVMJ-UHFFFAOYSA-N 2-bromobutanediamide Chemical compound NC(=O)CC(Br)C(N)=O DORVKAJYRZXVMJ-UHFFFAOYSA-N 0.000 claims description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- CFLAYISSADVCJH-UHFFFAOYSA-N 2,6-dimethylbenzoyl chloride Chemical compound CC1=CC=CC(C)=C1C(Cl)=O CFLAYISSADVCJH-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- CRCINIIYOHFQDM-UHFFFAOYSA-N 2-[2-(bromomethyl)-6-methylphenyl]-2-oxoacetyl chloride Chemical compound BrCC1=C(C(=O)C(=O)Cl)C(=CC=C1)C CRCINIIYOHFQDM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MKRSPMFGVLLSBV-UHFFFAOYSA-N 2,6-dimethylbenzoyl bromide Chemical compound CC1=CC=CC(C)=C1C(Br)=O MKRSPMFGVLLSBV-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1cccc(Cc2cccc(CBr)c2C(*)=O)c1C(*)=O Chemical compound Cc1cccc(Cc2cccc(CBr)c2C(*)=O)c1C(*)=O 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000013332 literature search Methods 0.000 description 1
- 150000005573 methoxybenzenes Chemical class 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a compound of 2-bromomethyl-6-methyl benzoylformylchloride / bromide as shown in a formula B and a preparation method thereof. The preparation method is as follows: in the presence of a catalyst of bromization reaction, a compound of 2,6-dimethylbenzoyl chloride/ bromide as shown in a formula A reacts with a bromide reagent in an inert organic solvent, wherein X is Cl or Br. The method of the invention has the advantages of higher product yield and purity, simple operation, mild reaction conditions and high selection of the bromization reaction; and is not only suitable for small-scale preparation in a laboratory, but also for industrial mass production.
Description
Technical field
The present invention relates to a kind of new compound and preparation method thereof, be specifically related to compound 2-bromomethyl-6-methyl benzoyl chloride/bromium and preparation method thereof.
Background technology
2-brooethyl-Benzoyl chloride/bromine compounds is the very important chemical intermediate of a class, can be converted into corresponding ester or acid amides etc., has very widely in industries such as medicine, agricultural chemicals, dyestuff, spices, makeup and uses.Ruano (N-Bromosuccinimide in Acetonitrile:A Mild and RegiospecificNuclear Brominating Reagent for Methoxybenzenes and Naphthalenes, J.Org.Chem.1995,60, p5328) etc. the people has reported take toluene as raw material, NBS is bromizating agent, methyl in the toluene is through single bromination reaction, the synthetic brooethyl benzene-like compounds that makes.But, when having two methyl to exist, one of them methyl is optionally carried out bromination reaction very difficult.By literature search, so far, have no the synthetic report of 2-bromomethyl-6-methyl benzoyl chloride/bromium.
Summary of the invention
Technical problem to be solved by this invention be for overcome prior art can not selectivity the defective of synthetic brooethyl benzene-like compounds, and a kind of new compound 2-bromomethyl-6-methyl benzoyl chloride/bromium is provided, but and a kind of method of this compound of high selectivity.
Compound 2-bromomethyl-6-methyl benzoyl chloride/bromium of the present invention is suc as formula shown in the B:
Wherein, X is Cl or Br.
The method of synthetic this compound of the present invention comprises the steps: in the inert organic solvents, under the effect of bromo-reaction catalyzer, will be suc as formula the compound 2 shown in the A, and 6-dimethyl benzoyl chloride/bromine reacts with bromide reagent and gets final product;
Wherein, X is Cl or Br.
Wherein, described bromide reagent is better is in liquid bromine, bromo succinic diamide (NBS) and the bromo glycolylurea one or more; What the consumption of described bromide reagent was better is suc as formula the compound 2 shown in the A, 0.6～1 times of the molar weight of 6-dimethyl benzoyl chloride/bromine and bromide reagent, and better is 0.7～1 times, best is 0.85～0.95 times; What described bromo-reaction catalyzer was better is the radical initiators such as azo isobutyl cyanogen (AIBN) and/or Benzoyl Peroxide (BPO); What the consumption of described bromo-reaction catalyzer was better is suc as formula the compound 2 shown in the A, 0.2%～0.7% of the molar weight of 6-dimethyl benzoyl chloride/bromine, and that better is 0.4-0.6%, best is 0.5～0.55%; What the temperature of described reaction was better is 40～100 ℃, and better is 60～80 ℃; The time of described reaction is by gas-chromatography GC follow-up control; What described inert solvent was better is methylene dichloride, chloroform, tetracol phenixin, 1, one or more in 2-ethylene dichloride, vinyl trichloride, sym.-tetrachloroethane, chlorobenzene, bromobenzene, fluorobenzene, dichlorobenzene, benzene and the cyanobenzene; The consumption of described inert solvent can be 5-10 times of 2,6-dimethyl benzoyl chloride/bromine weight.
Among the present invention, suc as formula the compound 2 shown in the A, 6-dimethyl benzoyl chloride/bromine can be by 2,6-mesitylenic acid and sulfur oxychloride or phosphorus tribromide direct reaction can make (reference: H.C.Martin, Ortho-benzyol-benzoyl chloride, J.Am.Chem.Soc., 1916,38,1142-1144).
Wherein, X is Cl, Br.
Equal commercially available the getting of agents useful for same and raw material among the present invention.
Positive progressive effect of the present invention is: compound 2-bromomethyl-6-methyl benzoyl chloride/bromium of the present invention can be converted into corresponding ester or acid amides etc., is applied to the industries such as medicine, agricultural chemicals, dyestuff, spices and makeup as important chemical intermediate.Synthetic method of the present invention is simple to operate, and reaction conditions is gentle, can realize the single bromination reaction of highly selective, the product yield that makes and purity higher, purity is more than 98%, and productive rate can reach more than 75%, be not only applicable to the laboratory and prepare on a small scale, but also be fit to industrialized production.Method of the present invention is 2 of China's abundant raw material, and the deep processing of 6-mesitylenic acid provides a kind of new way, has great economic worth..
Embodiment
Mode below by embodiment further specifies the present invention, but does not therefore limit the present invention among the described scope of embodiments.
Raw material 2,6-dimethyl benzoyl chloride/bromine is according to literature method (reference: H.C.Martin, Ortho-benzyol-benzoyl chloride, J.Am.Chem.Soc., 1916,38,1142-1144) made by 2,6-mesitylenic acid and sulfur oxychloride or phosphorus tribromide reaction.
Embodiment 1
Preparation 2-brooethyl-6-methyl benzoyl chloride
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl chloride (0.1mol), methylene dichloride (50mL), bromo succinic diamide (NBS) are (0.08mol), azo isobutyl cyanogen (AIBN) (0.0002mol) is stirred to GC in 40 ℃ after stirring and follows the tracks of the product peak area and no longer increase (4h).Steaming vibrating dichloromethane after reaction finishes, then to obtain product 2-brooethyl-6-methyl benzoyl chloride yield be 77% in distillation, purity is 98.2% (GC).
Embodiment 22-brooethyl-6-methyl benzoyl chloride
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl chloride (0.1mol), tetracol phenixin (40mL), NBS (0.09mol), Benzoyl Peroxide (BPO) (0.0002mol), azo isobutyl cyanogen (AIBN) (0.0002mol) is stirred to GC in 70 ℃ after stirring and follows the tracks of the product peak area and no longer increase (5h).Boil off the tetrachloro charcoal after reaction finishes, then to obtain product 2-brooethyl-6-methyl benzoyl chloride yield be 87% in distillation, and purity is 98.0% (GC).
Embodiment 3 2-brooethyl-6-methyl benzoyl chloride
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl chloride (0.1mol), 1,2-ethylene dichloride (60mL), bromo glycolylurea (0.095mol), AIBN (0.0005mol), being stirred to GC tracking product peak area in 70 ℃ after stirring no longer increases (4h).Boil off 1,2-ethylene dichloride after reaction finishes, then to obtain product 2-brooethyl-6-methyl benzoyl chloride yield be 89% in distillation, and purity is 98.6% (GC).
Embodiment 42-brooethyl-6-methyl benzoyl chloride
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl chloride (0.1mol), dichlorobenzene (60mL), liquid bromine (0.1mol), AIBN (0.0006mol), being stirred to GC tracking product peak area in 90 ℃ after stirring no longer increases (6h).Boil off chlorobenzene after reaction finishes, then to obtain product 2-brooethyl-6-methyl benzoyl chloride yield be 92% in distillation, and purity is 98.8% (GC).
Embodiment 52-brooethyl-6-methyl benzoyl chloride
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl chloride (0.1mol), bromobenzene (60mL), NBS (0.085mol), BPO (0.0006mol), being stirred to GC tracking product peak area in 100 ℃ after stirring no longer increases (5h).Boil off fluorobenzene after reaction finishes, then to obtain product 2-brooethyl-6-methyl benzoyl chloride yield be 92% in distillation, and purity is 98.9% (GC).
Embodiment 62-brooethyl-6-toluyl bromine
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl bromide (0.1mol), chlorobenzene (30mL), cyanobenzene (30mL), NBS (0.06mol), AIBN (0.0004mol), being stirred to GC tracking product peak area in 100 ℃ after stirring no longer increases (6h).Boil off chlorobenzene after reaction finishes, then to obtain product 2-brooethyl-6-toluyl bromine yield be 95% in distillation, and purity is 99.2% (GC).
Embodiment 72-brooethyl-6-toluyl bromine
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl bromide (0.1mol), chloroform (70mL), bromo glycolylurea (0.1mol), BPO (0.0006mol), being stirred to GC tracking product peak area in 100 ℃ after stirring no longer increases (4h).Boil off the tetrachloro charcoal after reaction finishes, then to obtain product 2-brooethyl-6-toluyl bromine yield be 91% in distillation, and purity is 98.5% (GC).
Embodiment 82-brooethyl-6-toluyl bromine
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl bromide (0.1mol), benzene (40mL), NBS (0.098mol), AIBN (0.0006mol), being stirred to GC tracking product peak area in 80 ℃ after stirring no longer increases (6h).Boil off benzene after reaction finishes, then to obtain product 2-brooethyl-6-toluyl bromine yield be 93% in distillation, and purity is 98.7% (GC).
Embodiment 92-brooethyl-6-toluyl bromine
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl bromide (0.1mol), fluorobenzene (50mL), NBS (0.lmol), BPO (0.0005mol), being stirred to GC tracking product peak area in 100 ℃ after stirring no longer increases (5h).Boil off fluorobenzene after reaction finishes, then to obtain product 2-brooethyl-6-toluyl bromine yield be 90% in distillation, and purity is 99.5% (GC).
Embodiment 102-brooethyl-6-toluyl bromine
Under the room temperature, in reaction flask, add 2,6-dimethyl benzoyl bromide (0.1mol), 1,1,2-trichloroethane (30mL), 1,1,2,2-tetrachloroethane (30mL), liquid bromine (0.099mol), AIBN (0.0007mol), being stirred to GC tracking product peak area in 60 ℃ after stirring no longer increases (6h).Boil off vinyl trichloride after reaction finishes, then to obtain product 2-brooethyl-6-toluyl bromine yield be 90% in distillation, and purity is 99.2% (GC).
Claims (7)
1. suc as formula the synthetic method of the compound 2-bromomethyl-6-methyl benzoyl chloride/bromium shown in the B, it is characterized in that: in the inert organic solvents, under the effect of bromo-reaction catalyzer, will be suc as formula the compound 2 shown in the A, 6-dimethyl benzoyl chloride/bromine and bromide reagent reaction get final product;
Wherein, X is Cl or Br; Described bromide reagent is one or more in liquid bromine, bromo succinic diamide and the bromo glycolylurea; Described bromo-reaction catalyzer is azo isobutyl cyanogen and/or Benzoyl Peroxide.
2. the method for claim 1 is characterized in that: the consumption of described bromide reagent is for suc as formula the compound 2 shown in the A, 0.6～1 times of the molar weight of 6-dimethyl benzoyl chloride/bromine.
3. method as claimed in claim 2 is characterized in that: the consumption of described bromide reagent is for suc as formula the compound 2 shown in the A, the molar weight of 6-dimethyl benzoyl chloride/bromine 0.85～0.95 times.
4. the method for claim 1 is characterized in that: the consumption of described bromo-reaction catalyzer is for suc as formula the compound 2 shown in the A, 0.2%～0.7% of the molar weight of 6-dimethyl benzoyl chloride/bromine.
5. the method for claim 1, it is characterized in that: the temperature of described reaction is 40～100 ℃.
6. method as claimed in claim 5, it is characterized in that: the temperature of described reaction is 60～80 ℃.
7. the method for claim 1, it is characterized in that: described inert solvent is methylene dichloride, chloroform, tetracol phenixin, 1,2-ethylene dichloride, 1,1,2-trichloroethane, 1,1, in 2,2-tetrachloroethane, chlorobenzene, bromobenzene, fluorobenzene, dichlorobenzene, benzene and the cyanobenzene one or more.
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| CN102417448B (en) * | 2011-08-18 | 2014-09-17 | 山东凯盛新材料有限公司 | Closed continuous production process of high-purity and high-melting point aromatic acyl chloride tablet product |
| CN106905135A (en) * | 2017-03-20 | 2017-06-30 | 上海应用技术大学 | A kind of preparation method to bromomethyl phenylacetic acid |
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| Title |
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| The Chlorination and Bromination of the Toluic Acids and the Preparation of the Phthalaldehydic Acids;William Davies et al.;《J.Chem.Soc.》;19220101;第2202-2215页 * |
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