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1. (WO2018032796) NOVEL 2-FLUOROCYCLOPROPANE CARBOXYLIC ACID SYNTHESIS METHOD

Pub. No.:    WO/2018/032796    International Application No.:    PCT/CN2017/081892
Publication Date: Fri Feb 23 00:59:59 CET 2018 International Filing Date: Wed Apr 26 01:59:59 CEST 2017
IPC: C07C 51/00
C07C 61/15
Applicants: CHEN-STONE(GUANGZHOU) CO., LTD.
广州康瑞泰药业有限公司
Inventors: LAI, Yingjie
赖英杰
WANG, Xuyan
王绪炎
Title: NOVEL 2-FLUOROCYCLOPROPANE CARBOXYLIC ACID SYNTHESIS METHOD
Abstract:
Disclosed is a novel 2-fluorocyclopropane carboxylic acid synthesis method, comprising the following steps: 1) reacting 1,1-dichloro-1-fluoroethane with thiophenol in the presence of alkali to produce a phenyl sulfide intermediate; 2) carrying out an oxidization reaction on the phenyl sulfide intermediate and oxone; 3) carrying out an elimination reaction on a product obtained in step 2) in the presence of alkali to obtain 1-fluorine-1-phenylsulfonyl ethane; 4) carrying out an addition reaction on the 1-fluorine-1-phenylsulfonyl ethane and ethyl diazoacetate in the presence of a catalyst to obtain a cyclopropane intermediate; and 5) carrying out an elimination reaction on the cyclopropane intermediate in the presence of alkali, and then acidizing to obtain 2-fluorocyclopropane carboxylic acid. The synthetic route is short, the materials are bulk commodities, cheap and easy to get, oxone is used to replace a commonly used mCPBA agent, the process is safely amplified, the reaction yield is increased, the production cost is greatly lowered, and the operation is simple.