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Preparation method of 2-(4-bromomethylphenyl) propionic acid

A technology of bromomethylphenyl and phenylpropionic acid, applied in the field of 2-propionic acid preparation, can solve the problems of complex production process, high production cost, low yield of finished products and the like, and achieves simple production process, low production cost, low pollution effect

Active Publication Date: 2015-07-01
ZHEJIANG BOJU NEW MATERIALS CO LTD
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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 of 2-(4-bromomethylphenyl) propionic acid
  • Preparation method of 2-(4-bromomethylphenyl) propionic acid
  • Preparation method of 2-(4-bromomethylphenyl) propionic acid

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Embodiment 1

[0027] The preparation method of the present embodiment 2-(4-bromomethylphenyl)propionic acid comprises 2-phenylpropionitrile preparation stage, 2-phenylpropionic acid preparation stage and 2-(4-bromomethylphenyl) Propionic acid stage, the specific steps are as follows:

[0028] 1) 2-phenylpropionitrile preparation stage

[0029] Add phenylacetonitrile: dimethyl carbonate: potassium carbonate at a molar ratio of 10:40:2 into a dry autoclave, slowly heat up to 180°C under stirring, keep the pressure below 2MPa, and keep warm for 30 hours to complete the reaction; liquid through pressure filtration, washing the reaction solution to neutrality, then distilling off excess dimethyl carbonate, and high vacuum rectification to obtain 2-phenylpropionitrile;

[0030] 2) 2-phenylpropionic acid preparation stage

[0031] Add liquid caustic soda: water: 2-phenylpropionitrile in 2:1:1 parts by weight to the hydrolysis reaction kettle, then heat up to 95°C, stir, reflux for 15 hours, cool...

Embodiment 2

[0035] The preparation method of the present embodiment 2-(4-bromomethylphenyl)propionic acid comprises 2-phenylpropionitrile preparation stage, 2-phenylpropionic acid preparation stage and 2-(4-bromomethylphenyl) Propionic acid stage, the specific steps are as follows:

[0036] 1) 2-phenylpropionitrile preparation stage

[0037] Add phenylacetonitrile: dimethyl carbonate: potassium carbonate at a molar ratio of 5:30:3 into a dry autoclave, slowly heat up to 220°C under stirring, control the pressure below 2.5MPa, and keep it warm for 20 hours to complete the reaction; The reaction solution is filtered through pressure, washed with water to neutrality, and then excess dimethyl carbonate is removed by distillation, and high vacuum rectification is carried out to obtain 2-phenylpropionitrile;

[0038] 2) 2-phenylpropionic acid preparation stage

[0039] Add liquid caustic soda: water: 2-phenylpropionitrile in 5:2:1 parts by weight to the hydrolysis reaction kettle, then raise ...

Embodiment 3

[0043] The preparation method of the present embodiment 2-(4-bromomethylphenyl)propionic acid comprises 2-phenylpropionitrile preparation stage, 2-phenylpropionic acid preparation stage and 2-(4-bromomethylphenyl) Propionic acid stage, the specific steps are as follows:

[0044] 1) 2-phenylpropionitrile preparation stage

[0045] Add phenylacetonitrile: dimethyl carbonate: potassium carbonate at a molar ratio of 2:35:3.5 into a dry autoclave, slowly heat up to 250°C under stirring, keep the pressure below 4MPa, and keep warm for 15 hours to complete the reaction; Liquid was removed by pressure filtration to remove solid potassium carbonate and washed the reaction solution to neutrality, then distilled to remove excess dimethyl carbonate, and high vacuum rectification obtained 2-phenylpropionitrile;

[0046] 2) 2-phenylpropionic acid preparation stage

[0047] Add liquid caustic soda: water: 2-phenylpropionic acid in 7:3:1 parts by weight to the hydrolysis reaction kettle, th...

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Abstract

The invention discloses a preparation method of 2-(4-bromomethylphenyl) propionic acid. The preparation method is characterized by comprising a preparation stage of 2-phenyl propionitrile, a preparation stage of 2-phenyl propionic acid and a preparation stage of 2-(4-bromomethylphenyl) propionic acid. The preparation stage of 2-phenyl propionitrile comprises the following steps: mixing benzyl cyanide, dimethyl carbonate and potassium carbonate; heating to 100-300 DEG C and carrying out thermal reaction for 5-50h under the pressure of 0.5-6MPa; and by the end of the reaction, carrying out filter pressing and rinsing to be neutral; distilling to removal excessive dimethyl carbonate; and carrying out high-vacuum rectification to obtain 2-phenyl propionitrile. Compared with the prior art, the preparation method disclosed by the invention has the following advantages and effects that the main raw material is benzyl cyanide which is subjected to methylation, hydrolysis reaction and bromomethylation to finally obtain the finished product; the purity of the finished product is high and the yield is up to 90% or above; and in addition, the preparation method has the advantages of simple production process, low production cost and low environment pollution.

Description

technical field [0001] The invention relates 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, and loxoprofen sodium belongs to the new type of non-steroidal anti-inflammatory drugs of aryl propionic acid. It has the best analgesic, anti-inflammatory and anti-rheumatic effects among 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 launched by Sankyo Pharmaceutical Co., Ltd. in Japan in 1986. It has been launched in Japan, South Korea, Europe, America and many other countries, with a strong growth momentum. According to statistics, the market sales in 1992 reached 180 million US dollars, and the sales in Japan in 1994 reached 25 billion yen, which belonged to the top 20 drugs ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/58C07C51/363
CPCC07C51/08C07C51/363C07C253/30C07C57/58C07C57/30C07C255/33
Inventor 龚华银周俊周邦福
Owner ZHEJIANG BOJU NEW MATERIALS CO LTD
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