Thionyl Chloride → 3-(Chloromethyl)-2-methylpyridine

Participants

Reaction Steps

To a stirred solution of 3-hydroxymethyl-2-methylpyridine (1.00 g, 8.13 mmol) from step 1 above in CH2Cl2 (40 mL) at ambient temperature was added SOCl2 (9.5 g, 80 mmol). The mixture was stirred for 4 h, and the solvent and excess SOCl2 were evaporated under reduced pressure. The residue was partitioned between CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was separated, and the aqueous layer was washed with additional CH2 Cl2 (2×40 mL). The combined organic layers were evaporated under reduced pressure to give 3-chloromethyl-2-methyl-pyridine as a solid which was used in the next step without purification (TLC: Rf = 0.85 (95:5 CH2Cl2 :MeOH); FAB MS m/z 142 (M+ +H)).

Provenance & Evidence