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

Participants

Reaction Steps

The crude of 2-(chloromethyl)-3-(methoxycarbonyl)pyridine-1-oxide (20 g, 99.5 mmol) was added in small portion to POCl3 (200 g) at room temperature. The mixture was refluxed for 3 hours before it was concentrated in vacuo. The residue was poured into ice-water, neutralized with NaHCO3 solution, and extracted with AcOEt (125 mL×3). The combined organic layers were concentrated to give the crude title product (17 g, yield 78%), which was used in the next step reaction without further purification.

Provenance & Evidence