Abstract
[^14^C] Aniline hydrogen sulphate was acetylated, and the acetanilide obtained was chlorinated with N‐chlorosuccinimide to 2‐chloro, 4‐chloro‐ and 2, 4‐dichloroacet[^14^C] anilide. The labelled 2‐ and 4‐chloroacet[^14^C] anilides were hydrolyzed and treated with aluminium chloride, hydrogen chloride and chlorine in dry dichloromethane to give the major products 2, 5‐dichloro‐ and 3, 4‐dichloro [^14^C] aniline. The labelled 2, 3‐dichloro‐ and 2,3, 6‐trichloroanilines were obtained as minor products from the chlorination of 2‐chloro [^14^C] aniline, likewise 2,4, 5‐trichloroaniline was obtained from 4‐chloro [^14^C] aniline. The [^14^C] anilines prepared were coupled with benzene, 1, 4‐dichloro‐, 1, 2‐dichloro or 1, 3‐dichlorobenzene to give 4‐chloro‐, 2, 3′,4′, 5‐tetrachloro‐, 2, 3, 3′, 4′ ‐ tetrachloro‐, 3,3′, 4,4′‐tetrachloro‐, 2, 2′, 5,5′‐tetrachloro‐, 2, 2′, 3,3′‐tetrachloro‐, 2, 2′, 3, 5′, 6‐pentachloro‐, 2, 2′, 4, 4′, 5‐pentachloro‐ and 2, 3′,4, 5, 5′‐pentachloro[^14^C]biphenyl.
3, 4‐Dichloro [^14^C] aniline and biphenyls prepared from this aniline were found to be contaminated by bromoanalogues. The origin of these have been studied.