Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 144-150.DOI: 10.6023/cjoc201810022 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞



付晓林a, 孙岩b, 赵志刚a, 郭勇b, 陈庆云b, 念保义c   

  1. a 西南民族大学化学与环境保护工程学院 成都 610041;
    b 中国科学院上海有机化学研究所 上海 200032;
    c 三明学院三明氟化工产业技术研究院 三明 365004
  • 收稿日期:2018-10-18 修回日期:2018-11-24 发布日期:2018-11-30
  • 通讯作者: 孙岩, 赵志刚;
  • 基金资助:


Synthesis of Alkyl Sulfate from α-Trifluoromethylbenzylbromide—An Extension of Sulfinatodehalogenation

Fu Xiaolina, Sun Yanb, Zhao Zhiganga, Guo Yongb, Chen Qingyunb, Nian Baoyic   

  1. a College of Chemistry & Environment Protection Engineering, Southwest Minzu University, Chengdu 610041;
    b College of Chemistry & Environment Protection Engineering, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    c Sanming Institute of Fluorochemical Industry, Sanming University, Sanming 365004
  • Received:2018-10-18 Revised:2018-11-24 Published:2018-11-30
  • Contact: 10.6023/cjoc201810022;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21737004, 21672239, 21421002) and the Sanming Institute of Fluorochemical Industry (Nos. FCIT201704GR, FCIT201705GR, FCIT201701BR).

The sulfinatodehalogenation reaction is a common method of introducing a fluoroalkyl group. In this paper, the reaction of α-trifluoromethylbenzyl bromide under sulfinatodehalogenation conditions was investigated. It was found that the product was an sodium alkyl sulfate (ArCH(CF3)OSO3Na) instead of an sodium alkyl sulfinate (ArCH(CF3)SO2Na) which was normal produced. α-Trifluoromethylbenzyl bromide did not react with the olefin after its generation of a radical intermediate under sulfinatodehalogenation conditions even though an olefin was presented. Instead, the reaction directly gave an alkyl sulfinate, and then oxidized by air to provide a product as an alkyl sulfate.

Key words: Trifiluoromethyl, free radical, sulfinatodehalogenation, alkyl sulfate