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2-bromomethyl-6-methyl benzoyl chloride/bromium and preparation method thereof

A technology of methylbenzoyl chloride and dimethylbenzoyl, which is applied in the field of new compounds and their preparation, can solve the problem of inability to selectively synthesize bromomethylbenzene compounds, and achieve great economic value, yield and purity High, easy-to-operate effect

Active Publication Date: 2009-03-11
CHINA GATEWAY PHARMA DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by this invention is to provide a new compound, 2-bromomethyl-6-methylbenzoyl chloride / bromine, and a A kind of method that can synthesize this compound with high selectivity

Method used

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  • 2-bromomethyl-6-methyl benzoyl chloride/bromium and preparation method thereof
  • 2-bromomethyl-6-methyl benzoyl chloride/bromium and preparation method thereof
  • 2-bromomethyl-6-methyl benzoyl chloride/bromium and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Preparation of 2-bromomethyl-6-methylbenzoyl chloride

[0020] At room temperature, add 2,6-dimethylbenzoyl chloride (0.1mol), dichloromethane (50mL), bromosuccinamide (NBS) (0.08mol), azoisobutylcyanide (AIBN ) (0.0002mol), stirred evenly and then stirred at 40°C until the peak area of ​​the product was no longer increased by GC tracking (4h). After the reaction was finished, dichloromethane was distilled off, and then the product 2-bromomethyl-6-methylbenzoyl chloride was obtained by distillation with a yield of 77% and a purity of 98.2% (GC).

Embodiment 2

[0021] Example 2 2-bromomethyl-6-methylbenzoyl chloride

[0022] At room temperature, add 2,6-dimethylbenzoyl chloride (0.1mol), carbon tetrachloride (40mL), NBS (0.09mol), benzoyl peroxide (BPO) (0.0002mol) to the reaction flask, Azoisobutyrocyanide (AIBN) (0.0002mol), stirred evenly and then stirred at 70°C until the peak area of ​​the product no longer increased after GC tracking (5h). After the reaction, the carbon tetrachloride was evaporated, and then the product 2-bromomethyl-6-methylbenzoyl chloride was distilled with a yield of 87% and a purity of 98.0% (GC).

Embodiment 3

[0023] Example 3 2-bromomethyl-6-methylbenzoyl chloride

[0024] At room temperature, add 2,6-dimethylbenzoyl chloride (0.1mol), 1,2-dichloroethane (60mL), bromohydantoin (0.095mol), AIBN (0.0005mol) into the reaction flask, After stirring evenly, stir at 70°C until the peak area of ​​the product does not increase after GC tracking (4h). After the reaction was completed, 1,2-dichloroethane was evaporated, and then the product 2-bromomethyl-6-methylbenzoyl chloride was obtained by distillation with a yield of 89% and a purity of 98.6% (GC).

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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 [0001] The invention relates to a novel compound and a preparation method thereof, in particular to the compound 2-bromomethyl-6-methylbenzoyl chloride / bromine and a preparation method thereof. Background technique [0002] 2-Bromomethyl-benzoyl chloride / bromine compounds are very important chemical intermediates, which can be converted into corresponding esters or amides, etc., and are widely used in medicine, pesticides, dyes, fragrances, cosmetics and other industries . Ruano (N-Bromosuccinimide in Acetonitrile: A Mild and Regiospecific Nuclear Brominating Reagent for Methoxybenzenes and Naphthalenes, J.Org.Chem.1995, 60, p5328) et al reported that using toluene as a raw material, NBS as brominating agent, toluene in toluene The bromomethyl benzene compounds were synthesized by monobromination reaction. However, when there are two methyl groups, it is difficult to selectively brominate one of them. Through literature search, so far, there is no report o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C63/70C07C51/62
Inventor 刘国斌李原强牟英波刘长喜
Owner CHINA GATEWAY PHARMA DEV CO LTD
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