Water → 6-Bromo-5-fluoropicolinic Acid

Participants

Reaction Steps

To 2-bromo-3-fluoro-6-methylpyridine (2.0 g, 10.58 mmoles) in H2O (30 mL) was added potassium permanganate (1.67 g, 10.58 mmoles). The solution was heated at 100° C. for 5 hours at which time more potassium permanganate (1.67 g, 10.58 mmoles) was added. After heating for an additional 48 hours the material was filtered through celite (4 cm×2 inches) and rinsed with H2O (150 mL). The combined aqueous was acidified with 1N HCl to pH4, extracted with ethyl acetate (200 mL), washed with NaCl(sat.), dried over MgSO4, filtered and concentrated to yield 6-bromo-5-fluoropicolinic acid (17%) as a white solid. LCMS (m/z): 221.9 (MH+); LC Rt=2.05 min.

Provenance & Evidence