N-Trihalomethyl derivatives of benzimidazole, benzotriazole and indazole

1-Chlorodifluoromethyl- and 1-trifluoromethyl-substituted 2-methylbenzimidazoles and benzotriazoles were obtained by chlorination of the corresponding methyl 1-azoledithiocarboxylates and subsequent fluorination of the resulting 1-trichloromethyl derivatives. The condensation of N-sodium salts of 2-alkylbenzimidazoles and indazole with CF2Br2 was shown to afford the corresponding 1-bromodifluoromethylated compounds.