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

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.

Keywords:

• Aniline
• N-chlorosuccinimide
• chlorination
• diazonium

ACKNOWLEDGMENTS

The financial support of Timothy I. Mahoney (NAWCWD Pilot Plant) is gratefully acknowledged. Thanks to Juanita K. Morton (NAWCWD) for assistance in purchasing the hypophosporous acid. Thanks to Ann M. Moorehead, Cynthia M. Kitchens, and the staff of the NAWC Technical Library (China Lake) for obtaining Ref. 9.