Citation: Fu Xiaolin, Sun Yan, Zhao Zhigang, Guo Yong, Chen Qingyun, Nian Baoyi. Synthesis of Alkyl Sulfate from α-Trifluoromethylbenzylbromide—An Extension of Sulfinatodehalogenation[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 144-150. doi: 10.6023/cjoc201810022 shu

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

Fu Xiaolin ^a ,
Sun Yan ^b,, ,
Zhao Zhigang ^a,, ,
Guo Yong ^b ,
Chen Qingyun ^b ,
Nian Baoyi ^c

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

Corresponding author: Sun Yan, sunyan@sioc.ac.cn Zhao Zhigang, zzg63129@163.com
Received Date: 18 October 2018
Revised Date: 24 November 2018
Available Online: 30 January 2018
Fund Project: the Sanming Institute of Fluorochemical Industry FCIT201701BRProject 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 Sanming Institute of Fluorochemical Industry FCIT201705GRthe National Natural Science Foundation of China 21672239the National Natural Science Foundation of China 21737004the Sanming Institute of Fluorochemical Industry FCIT201704GRthe National Natural Science Foundation of China 21421002

Figures(3)

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.
- Trifiluoromethyl,
- free radical,
- sulfinatodehalogenation,
- alkyl sulfate
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