6-Chloro-2-chloromethylpyridine is prepared from 6-chloro-2-methylpyridine by a route in which the 2-Me substituent was successively converted to 2-acetoxymethyl, 2-hydroxymethyl and finally to the required 2-chloromethyl substituent. Attempts to simultaneously monochlorinate the Me group and reduce the N-oxide function of 6-chloro-2-methylpyridine- N-oxide with methanesulphonyl chloride and p-toluenesulphonyl chloride gave only very ...