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Synthesis method for 2-(2-bromoethyl)benzoic acid methyl ester

A technology of vinyl methyl benzoate and formaldehyde methyl benzoate, which is applied in the field of synthesis of 2-methyl benzoate and can solve problems such as unfavorable industrial production

Inactive Publication Date: 2013-01-02
CGENETECH (SUZHOU CHINA) CO LTD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0002] Methyl 2-(2-bromoethyl)benzoate is an important chemical intermediate and is an intermediate of many pharmaceutical or chemical products, but it has always been produced in small batches, which is not conducive to industrial production

Method used

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  • Synthesis method for 2-(2-bromoethyl)benzoic acid methyl ester
  • Synthesis method for 2-(2-bromoethyl)benzoic acid methyl ester

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Embodiment

[0012] Methyltriphenylphosphine hydriodide (36.9 g, 91.5 mmol) was suspended in THF (500 mL), -50 o 1.6 mol per liter of n-butyllithium (57.2 ml, 91.5 mmol) was added dropwise at 0°C. After the addition, the reaction mixture was slowly warmed to room temperature and stirred for an hour, then continued to cool to -70 o C. A solution of methyl 2-formaldehyde benzoate (10 g, 61 mmol) in tetrahydrofuran (150 ml) was added dropwise to the above solution. After the addition, the temperature was slowly raised to room temperature and stirred overnight. After the reaction solution was concentrated, 500 ml of water was added. , extracted twice with dichloromethane, the organic phase was dried and concentrated to obtain an oil, and a colorless oily product, methyl 2-vinylbenzoate (7 g, yield 70%) was obtained after silica gel column chromatography.

[0013] Methyl 2-vinylbenzoate (7 g, 43.2 mmol) obtained in the previous step was dissolved in tetrahydrofuran (45 ml), cooled to 0°C, and ...

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Abstract

The present invention discloses a synthesis process for 2-(2-bromoethyl)benzoic acid methyl ester. According to the synthesis process, easily-available 2-formyl benzoic acid methylester is adopted as a raw material, and reacts with methyl triphenylphosphine hydroiodide in the presence of a strong base to obtain 2-methyl vinylbenzoate; the 2-methyl vinylbenzoate reacts with a borane dimethyl sulfide complex; 2-(2-hydroxyethyl)benzoic acid methyl ester is produced under conditions of sodium hydroxide and hydrogen peroxide; and finally the 2-(2-hydroxyethyl)benzoic acid methyl ester is converted into the 2-(2-bromoethyl)benzoic acid methyl ester under conditions of triphenylphosphine and carbon tetrabromide.

Description

technical field [0001] The invention relates to a synthesis process of 2-(2-bromoethyl)methyl benzoate, which belongs to the technical fields of medicine and chemical industry. Background technique [0002] Methyl 2-(2-bromoethyl)benzoate is an important chemical intermediate, and is an intermediate of many pharmaceutical or chemical products, but it has always been produced in small batches, which is not conducive to industrial production. Contents of the invention [0003] The present invention takes easy-to-get methyl 2-formaldehyde benzoate as a raw material to react with methyl triphenylphosphine hydriodide under a strong base to obtain methyl 2-vinyl benzoate and then react with borane dimethyl sulfide After the reaction of the ether complex, 2-(2-hydroxyethyl) methyl benzoate is generated under sodium hydroxide and hydrogen peroxide conditions, and finally converted into 2-(2- bromoethyl) methyl benzoate. [0004] The above-mentioned chemical reaction and the reac...

Claims

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Application Information

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IPC IPC(8): C07C69/78C07C67/307
Inventor 汤木林丁炬平张仁延余强
Owner CGENETECH (SUZHOU CHINA) CO LTD
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