Thionyl Chloride → 3-Chloromethyl-4-trifluoromethylpyridine hydrochloride

Participants

Reaction Steps

To a stirred solution of 3-hydroxymethyl-4-trifluoromethylpyridine (1.11 g, 6.27 mmol) from step 1 above in CH2Cl2 (20 mL) at 0° C. was added SOCl2 (0.89 g, 7.5 nmuol) in CH2Cl2 (10 mL). The mixture was allowed to warm to room temperature and stirred for 1 h, and the solvent and excess SOCl2 were evaporated under reduced pressure. The residue was concentrated from cyclohexane (3-) to give 3-chloromethyl-4-trifluoromethylpyridine hydrochloride as a solid which was used in the next step without purification (TLC: Rf = 0.75 (1:1 hexane:EtOAc)).

Provenance & Evidence