m-Chloroperbenzoic acid → 2-Bromo-3-fluoropyridine 1-oxide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-3-fluoropyridine (1.0 g, 5.7 mmol) and 3-chloroperbenzoic acid (1.5 g, 7.4 mmol) in chloroform (3.5 mL) was stirred at 50° C. for 18 hours, cooled down to room temperature and filtered. The filtrate was concentrated under reduced pressure to give a residue that was purified by flash chromatography (Si—PPC, MeOH:EtOAc, gradient 0:100 to 5:95) to give 2-Bromo-3-fluoropyridine 1-oxide as a white solid (878 mg, 80%). 1H NMR (400 MHz, CHCl3-d): δ 8.25 (dt, J=6.6, 1.3 Hz, 1H); 7.25-7.17 (m, 1 H); 7.06 (ddd, J=8.7, 6.6, 1.3 Hz, 1 H).

Provenance & Evidence