Methanol → (4-Chloro-3-fluoropyridin-2-yl)methanol

Participants

Reaction Steps

Trifluoroacetic anhydride (16.18 ml) was added dropwise at 10°-15° to a solution of 2-methyl-3-fluoro-4-chloropyridine-N-oxide (6.17 g) in dichloromethane (50 ml). After three days at room temperature, methanol (30 ml) was added to the cooled solution. The excess solvent was removed and the residue dissolved in water. After basifying (NaOH), the solution was extracted with dichoromethane. The extracts were dried (K2CO3) and evaporated to dryness to give a solid which was purified by column chromatography (silica gel; 1% MeOH/CHCl3) to give 2-hydroxymethyl-3-fluoro-4-chloropyridine (3.8 g) m.p. indeterminate)

Provenance & Evidence