A Facile Synthesis of Isomeric C-(2,2,2-Trifluoroethyl)anilines

In memory of Prof. L. M. Yagupolskii - a father of modern fluoroorganic chemistry

Abstract

Three isomers of C-(2,2,2-trifluoroethyl)aniline were prepared on a multigram scale from readily available nitrophenylacetic acids­ in two steps. First, the carboxy groups of the latter were converted into the trifluoromethyl moieties by treatment with sulfur tetra­fluoride. The obtained 2,2,2-trifluoroethyl-substituted nitrobenzenes were reduced catalytically into the corresponding anilines.

Key words

amines - trifluoromethyl group - fluorine - sulfur tetrafluoride - hydrogenation

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