Add time:09/06/2019 Source:sciencedirect.com
The preparation of 14C-labelled biphenyl, 2,5-dichlorobiphenyl, 2,4′,5-trichlorobiphenyl, 2,2′,4,5′-tetrachlorobiphenyl, 2′,3,4,4′,5-pentachlorobiphenyl, 2,2′,3,4,4′-pentachlorobiphenyl, 2,3,3′,4′,6-pentachlorobiphenyl and 2,2′,3,3′,6-pentachlorobiphenyl is described [14C]Aniline hydrogen sulfate used as a starting material was acetylated, chlorinated and deacetylated followed by coupling to benzene or an appropriate chlorobenzene to give the biphenyls labelled in the phenyl nuclei having chlorine atoms at the 4-, 2,4- or 2,3,6-positions, respectively. The structures of the labelled compounds were established by comparison with authentic samples among which 2′,3,4,4′,5- and 2,2′,3,4,4′-pentachlorobiphenyl were not earlier described.A simple method for the preparation of 2,3,6-trichloroacetanilide, unlabelled and labelled, was worked out. 2,6-Dichloroacetanilide in concentrated hydrochloric acid gave the meta substituted product when treated with chlorine.An improved thin layer chromatographic technique utilizing plates impregnated with certain tetraalkylammonium salts was used for separation of some of the labelled compounds prepared.
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