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3,3-gem-difluoro cyclobutanecarboxylic acid industrial preparation method

A technology of difluorocyclobutanecarboxylic acid and difluorocyclobutanecarboxylic acid, applied in the direction of carboxylate preparation, chemical instruments and methods, carboxylate/lactone preparation, etc. Reagents are expensive and other problems, to achieve the effect of low cost and reasonable reaction process selection

Inactive Publication Date: 2016-03-23
SHANGHAI STA PHARMA R&D CO LTD
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  • Application Information

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Problems solved by technology

[0009] The purpose of the present invention is to provide an industrialized preparation method of 3,3-gem-difluorocyclobutanecarboxylic acid, which mainly solves the technical problem that the raw materials and fluorinated reagents in the existing preparation method are expensive and cannot be produced on a large scale

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  • 3,3-gem-difluoro cyclobutanecarboxylic acid industrial preparation method

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Embodiment Construction

[0015] The following examples help to understand the present invention, but do not limit the content of the present invention.

[0016] Synthesis of methyl 2,2-dichloro-3,3-difluorocyclobutanecarboxylate

[0017] Cool 1,1-dichloro-2,2-difluoroethylene (618g, 4.64mol) to -10-0°C, mix well with methyl acrylate (200g, 2.32mol), and add to the autoclave. Heat the reaction to 150° C., and react for 15-20 hours to obtain a reaction liquid containing the product.

[0018] Take 50g of the above reaction solution, adjust the pH value to 5-7 with sodium hydroxide, then concentrate under reduced pressure to 50-100mL, add 100mL of water, concentrate under normal pressure, collect the distillate, extract with dichloromethane (100mL*3), The organic phase was concentrated to obtain 16 g of fine product (yield 65-70%). NMR characterization 1 HNMR (CDCl 3 )9.78(1H,s), 3.23(1H,m), 3.10(1H,m), 2.80(1H,m).

[0019] 2-Chloro-3,3-difluoro-1-enecyclobutanecarboxylic acid

[0020] Prepare an...

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Abstract

The invention relates to a 3,3-gem-difluoro cyclobutanecarboxylic acid industrial preparation method. The method mainly solves the technical problem of existing preparing methods that the price of the raw material 3-oxo-cyclobutylcarboxylic acid or 3-methylenecyclobutane-carbonitrile and the price of the fluoro reagent DAST are high, and therefore large-scale production can not be conducted. According to the 3,3-gem-difluoro cyclobutanecarboxylic acid industrial preparation method, conventional methyl acrylate and 1,1-dichloro-2,2-difluoroethylene which are easy to obtain are taken as raw materials, and 3,3-gem-difluoro cyclobutanecarboxylic acid is obtained through addition, hydrolysis and hydrogenation. Please see the description for the chemical equation. The 3,3-gem-difluoro cyclobutanecarboxylic acid industrial preparation method is simple, practical and quite low in preparing cost.

Description

technical field [0001] The invention relates to a preparation method of 3,3-gem-difluorocyclobutane formic acid, in particular to a practical and effective industrial preparation method of 3,3-gem-difluorocyclobutane formic acid. Background technique [0002] 3,3-gem-difluorocyclobutanecarboxylic acid is a key intermediate for the preparation of some drugs, generally prepared with 3-oxocyclobutanecarboxylic acid as the starting material, and there are also a few literature reports using 3-oxocyclobutanenitrile as the starting material. Reaction schemes for starting materials. However, the above two raw materials are expensive, and the two synthetic methods are suitable for preparing a small amount of 3,3-gem-difluorocyclobutanecarboxylic acid in the laboratory. So far, no practical and effective method for the industrial preparation of 3,3-gem-difluorocyclobutanecarboxylic acid has been reported. [0003] Two commonly used preparation methods have been reported in the lite...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/36C07C61/15
CPCC07C67/347C07C51/09C07C51/36
Inventor 吴明遥杨洁郭威徐建平施峰郭盛骏
Owner SHANGHAI STA PHARMA R&D CO LTD
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