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Synthesis 2010(7): 1159-1165  
DOI: 10.1055/s-0029-1219232
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Synthesis of 1-Chloro-2,2,2-trifluoroethyl Sulfides

Yuriy Pustovit*a, Anatoliy Alexeenkoa, Sergii Trofymchuka, Oleg Lukin*b,c, Andrey A. Tolmachevb,c
a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmans’ka St. 5, 02094 Kiev, Ukraine
b National Taras Shevchenko University, ChemBioCenter, Volodymyrska St. 62, 01033 Kiev, Ukraine
c Enamine Ltd., A. Matrosova St. 23, 01103 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: oleg.lukin@mail.univ.kiev.ua;
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Publication History

Received 25 September 2009
Publication Date:
20 January 2010 (online)

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Abstract

A facile synthesis of structurally diverse 1-chloro-2,2,2-trifluoroethyl sulfides from readily available 1-bromo-1-chloro-2,2,2-trifluoroethane (Halothane®) and various aliphatic and aromatic thiols in the presence of sodium dithionite/sodium bicarbonate is described. The synthetic utility of the prepared sulfides is illustrated by the synthesis of biologically potent heterocycles and by their electrophilic reactions with thiophene.

Key words

thiols - radical reactions - alkylations - fluorinated compounds - sulfides