Phosphorus oxychloride → Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate

Participants

Reaction Steps

Methyl 2-(chloromethyl)pyridine-3-carboxylate 1-oxide (17.85 g, 89 mmol) was stirred in refluxing POCl3 (80 mL, 858 mmol) for 3 hours. Room temperature was attained and the reaction mixture poured into ice-water. The resulting beige precipitate was collected by filtration and purified by flash chromatography (silica, 2-20% ethyl acetate/hexanes) to afford the title compound as a white solid. 1H NMR (CDCl3, 600 MHz) δ 8.22 (d, 1H), 7.37 (d, 1H), 5.03 (s, 2H), 3.95 (s, 3H).

Provenance & Evidence