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Preparation method for 2-(4-brooethylphenyl) propionic acid

A technology of bromomethylphenyl and tolyl propionic acid is applied in the field of preparation of 2-(4-bromomethylphenyl) propionic acid, and can solve the problems of complex production process, high production cost, low yield of finished products and the like , to achieve the effect of simple production process, low production cost and low pollution

Inactive Publication Date: 2013-10-09
NANTONG TAITONG CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

my country has also started production and clinical application in recent years, but the production process of the existing technology is complex, the production cost is high, the pollution is large, and the yield of the finished product is low

Method used

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  • Preparation method for 2-(4-brooethylphenyl) propionic acid

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Effect test

Embodiment 1

[0016] The preparation method of 2-(4-bromomethylphenyl)propionic acid, including p-tolyl-2-chloro-1-one preparation stage, 2-p-tolylpropionic acid preparation stage and 2-(4-bromomethyl Phenyl)propionic acid stage, the specific steps are as follows:

[0017] (1), p-tolyl-2-chloro-1-one preparation stage

[0018] Add anhydrous aluminum trichloride:anhydrous toluene at a molar ratio of 1:1 to a dry acylation reaction kettle, cool to 0°C, and slowly add 2-chloropropionyl chloride in a molar ratio of 1 dropwise under stirring, dropwise The completion time is 2 hours, and the reaction is completed at a temperature of 0°C for 8 hours; put the hydrolysis kettle into ice water and stir slowly, put the reactants into the hydrolysis kettle, control the hydrolysis temperature at 1°C when discharging, and continue stirring for 30 minutes after discharging , and then static layering, the lower aluminum chloride aqueous solution is separated, the organic layer is washed with sodium chlori...

Embodiment 2

[0025] The preparation method of 2-(4-bromomethylphenyl)propionic acid, including p-tolyl-2-chloro-1-one preparation stage, 2-p-tolylpropionic acid preparation stage and 2-(4-bromomethyl Phenyl)propionic acid stage, the specific steps are as follows:

[0026] (1), p-tolyl-2-chloro-1-one preparation stage

[0027] Add anhydrous aluminum trichloride:anhydrous toluene at a molar ratio of 10:20 to the dry acylation reaction kettle, cool to 3°C, and slowly add 2-chloropropionyl chloride in a molar ratio of 5 under stirring, dropwise The completion time is 2.5 hours, and the reaction is completed at a temperature of 3°C for 8 hours; put the hydrolysis kettle into ice water and stir slowly, put the reactants into the hydrolysis kettle, control the hydrolysis temperature at 3°C ​​when discharging, and continue stirring for 30 minutes after discharging , and then static layering, the lower aluminum chloride aqueous solution is separated, the organic layer is washed with sodium chlorid...

Embodiment 3

[0033] The preparation method of 2-(4-bromomethylphenyl)propionic acid is characterized in that it comprises p-tolyl-2-chloro-1-one preparation stage, 2-p-tolylpropionic acid preparation stage and 2-(4 -bromomethylphenyl) propionic acid stage, the concrete steps are as follows:

[0034] (1), p-tolyl-2-chloro-1-one preparation stage

[0035] Add anhydrous aluminum trichloride:anhydrous toluene at a molar ratio of 20:30 to a dry acylation reaction kettle, cool to 5°C, and slowly add 2-chloropropionyl chloride at a molar ratio of 10 under stirring, dropwise The completion time is 3 hours, and the reaction is completed at a temperature of 5°C for 8 hours; put the hydrolysis kettle into ice water and stir slowly, put the reactants into the hydrolysis kettle, control the hydrolysis temperature at 5°C when discharging, and continue stirring for 30 minutes after discharging , and then static layering, the lower aluminum chloride aqueous solution is separated, the organic layer is was...

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Abstract

The invention relates to the technical field of 2-(4-brooethylphenyl) propionic acid, and in particular relates to a preparation method for 2-(4-brooethylphenyl) propionic acid. The preparation method comprises the following steps of: taking p-methylphenyl-2-chloro-1-ketone and 2-p-methylphenyl propionic acid as main raw materials, and finally preparing a finished product via a dry acylation reaction, a condensation reaction and a bromination reaction, wherein the finished product is high in purity and high in yield which is up to more than 98%, is one of key intermediates for synthesising loxoprofen sodium, and is clinically indicated to be the greatest in the effects of easing pain, resisting inflammation and resisting rheumatism within the presently known aryl propionic acid medicines, thus being greatly preferred by national and international experts and scholars, and promoted by the medical circle and patients. Additionally, the preparation method disclosed by the invention is simple in production process, low in production cost, and less in pollution.

Description

technical field [0001] The invention relates to the technical field of 2-(4-bromomethylphenyl)propionic acid, in particular to a preparation method of 2-(4-bromomethylphenyl)propionic acid. Background technique [0002] At present, 2-(4-bromomethylphenyl) propionic acid is one of the key intermediates for the synthesis of loxoprofen sodium, which belongs to the new type of non-steroidal anti-inflammatory drugs of aryl propionic acid, and it has been clinically shown that it It has the best analgesic, anti-inflammatory and anti-rheumatic effects among the currently known aryl propionic acid drugs, so it is favored by experts and scholars at home and abroad, as well as respected by the medical community and patients. This product was developed and marketed by Sankyo Pharmaceutical Co., Ltd. in Japan in 1986. It has been marketed in Japan, South Korea, Europe, America and many other countries, and its growth momentum is strong. According to statistics, the market sales in 1992...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/58C07C51/363
Inventor 储晓建
Owner NANTONG TAITONG CHEM TECH
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