Methyl iodide → 2-Chloro-3-methoxypyridine

To a stirred solution of 2-chloro-3-hydroxypyridine (25.4 g, 196 mmol) in dry DMF (250 mL), at 0° C., was added sodium methoxide (11.5 g, 213 mmol). After 5 min, the reaction mixture was allowed to warm to RT. After 1 hour, the mixture was cooled to 0° C. and iodomethane (24 mL, 386 mmol) was added. The reaction mixture was stirred at 0° C. for 5 minutes, before allowing to warm to RT. After 2 hours, the reaction mixture was concentrated under reduced pressure. The resultant residue was partitioned between diethyl ether and water. The aqueous phase was isolated and extracted twice with diethyl ether. The combined organic extracts were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (22.2 g, 79%) as an orange solid. LCMS (Method A): RT=2.76 min, [M+H]+=144/146.