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Preparation method for 4-(3-fluorine phenyl)-2,2-phenyl-5-(4-(methylmercapto-)phenyl) furan-3(2H)-ketone

A technology of fluorophenyl and methylthio, which is applied in the field of organic synthesis, can solve the problems of low product purity, complicated production methods, and high production costs, and achieve the effects of simple process, reduced production costs, and improved production efficiency

Inactive Publication Date: 2014-10-15
NANTONG HUAFENG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the prior art, the production method of 4-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H)-one is complicated, and the production cost High, and the yield is low, and the product purity is not high

Method used

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  • Preparation method for 4-(3-fluorine phenyl)-2,2-phenyl-5-(4-(methylmercapto-)phenyl) furan-3(2H)-ketone
  • Preparation method for 4-(3-fluorine phenyl)-2,2-phenyl-5-(4-(methylmercapto-)phenyl) furan-3(2H)-ketone
  • Preparation method for 4-(3-fluorine phenyl)-2,2-phenyl-5-(4-(methylmercapto-)phenyl) furan-3(2H)-ketone

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Embodiment

[0022] 1) Preparation of m-fluorophenylacetyl chloride (FPAC)

[0023] Add 305g m-fluorophenylacetic acid successively in a 1L three-necked flask. 500ml of thionyl chloride and 2ml of DMF, stirred and heated to reflux, the temperature was 110°C, the time was 4h, the reaction was completed, and the thionyl chloride was removed by atmospheric distillation, and the product at 64°C / 5mmHg and 320g wine red product were collected. The rate is 82.3%.

[0024] 2) Synthesis of 3-bromo-3-methyl-2-oxobutylcyanide (BBC)

[0025] 557g of BBB (2-bromo-2-methylpropionyl bromide) and 283g of trimethylsilyl cyanide were added to a 1L three-necked flask, the temperature was controlled at 85°C and the reaction was stirred for 3 hours, then cooled to room temperature and collected at 70°C / The product of 79mmHg is 384g, and the yield is 90.04%.

[0026] 3) 2-(3-fluorophenyl)-1-(4-(methylthio)phenyl)ethanone (FME)

[0027] In a 3L three-neck flask, add 2500ml of dichloromethane, quickly add (2...

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Abstract

The invention discloses a preparation method for 4-(3-fluorine phenyl)-2,2-phenyl-5-(4-(methylmercapto-)phenyl)furan-3(2H)-ketone. The preparation method comprises the following steps: m-fluorobenzene acetylchloride is generated under the existence of fluorobenzene acetic acid and thionyl chloride; 2-bromine-2-methyl propionyl-bromine is reacted with trimethyl cyanogen silane to generate 3-bromine-3-methyl-2-oxo butyl cyanide; m-fluorobenzene acetylchloride is reacted with thioanisole to generate 2-(3-fluorine phenyl)-1-(4-(methylmercapto-)phenyl) acetone under the existence of aluminium trichloride and dichloromethane; the 4-(3-fluorine phenyl)-2,2-phenyl-5-(4-(methylmercapto-)phenyl)furan-3(2H)-ketone is generated by the 2-(3-fluorine phenyl)-1-(4-( methylmercapto-)phenyl)acetone and the 3-bromine-3-methyl-2-oxo butyl cyanide; a best product is obtained through separation, crystallization, filtering and drying.

Description

technical field [0001] The present invention relates to an organic synthesis method, in particular to a 4-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H) - Process for the preparation of ketones. Background technique [0002] 4-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H)-one has strong inhibitory effect and good anti-inflammatory activity , can be used in medical, biological, chemical and other fields. In the prior art, the production method of 4-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H)-one is complicated, and the production cost High, and the yield is low, and the product purity is not high simultaneously. [0003] Therefore, in order to solve the above problems, a new technical solution is provided. Contents of the invention [0004] The object of the present invention is to provide a kind of technology simple, the product yield height 4-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3 (2H...

Claims

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Application Information

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IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 王德峰张耀兵石朗银石飞
Owner NANTONG HUAFENG CHEM
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