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Vol. 29 No. 1 (2017): Vol 29 Issue 1

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A Concise and Convenient Synthesis of 4-(Trifluoromethylthio)aniline

https://doi.org/10.14233/ajchem.2017.20138
Shunze Gong
School of Pharmaceutical and Life Sciences, Changzhou University, Changzhou, Jiangsu 213164, P.R. China *Corresponding author: Fax: +86 519 86334598; Tel: +86 519 86334597; E-mail: markxu@cczu.edu.cn
Xinhong Cai
School of Pharmaceutical and Life Sciences, Changzhou University, Changzhou, Jiangsu 213164, P.R. China *Corresponding author: Fax: +86 519 86334598; Tel: +86 519 86334597; E-mail: markxu@cczu.edu.cn
Hao Fu
School of Pharmaceutical and Life Sciences, Changzhou University, Changzhou, Jiangsu 213164, P.R. China *Corresponding author: Fax: +86 519 86334598; Tel: +86 519 86334597; E-mail: markxu@cczu.edu.cn
Defeng Xu*
School of Pharmaceutical and Life Sciences, Changzhou University, Changzhou, Jiangsu 213164, P.R. China *Corresponding author: Fax: +86 519 86334598; Tel: +86 519 86334597; E-mail: markxu@cczu.edu.cn

Asian Journal of Chemistry, Vol. 29 No. 1 (2017): Vol 29 Issue 1

Abstract

4-(Trifluoromethylthio)aniline, a key agricultural intermediate, can be synthesized from 4-nitrobromobenzene. First 4-nitrothioanisole was obtained by the methylthiotriazine of 4-nitrobromobenzene with sodium salt of methyl mercaptan in the presence of phase-transfer catalyst in a 91.4 % yield; then 4-(trifuroromethylthio)nitrobenzene was produced through chlorination in a 83.7 % yield and fluorination in a 86.3 % yield; finally the hydrogenation in the presence of Pd/C can afford 4-(trifluoromethylthio)aniline with a 98 % yield.

Keywords

Methylthiotriazine Chlorination Fluorination Hydrogenation Phase translation catalyst.
Gong, S., Cai, X., Fu, H., & Xu*, D. (2016). A Concise and Convenient Synthesis of 4-(Trifluoromethylthio)aniline. Asian Journal of Chemistry, 29(1), 91–93. https://doi.org/10.14233/ajchem.2017.20138
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