Synthesis and thiolation of 1,3-difluoro-2,4,6-trihaloanilines and benzenes

Three pentahaloanilines were prepared by stepwise halogenation of 3,5-difluoroaniline and were deaminated to form pentahalobenzenes. Alternatively, two pentahalobenzenes were obtained by lithiation followed by iodination of 1,3-difluoro-4,6-dihalobenzenes. Alkylthiolation reactions of pentahaloanilines and benzenes in Me2SO were investigated.