Chlorination of Aniline and Methyl Carbanilate by N-Chlorosuccinimide and Synthesis of 1,3,5-Trichlorobenzene

Author: Davis Matthew  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.39, Iss.6, 2009-01, pp. : 1100-1108

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Abstract

Aniline undergoes regioselective trichlorination by N-chlorosuccinimide (NCS) in acetonitrile in good yield. The product 2,4,6-trichoroaniline was converted into 1,3,5-trichlorobenzene by reduction of its diazonium salt. Reaction of the methyl carbamate of aniline with NCS gave only the 2,4-dichlorophenyl carbamate.