Water → 6-Bromo-3-fluoropyridine-2-carboxylic acid

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Reaction Conditions

Reaction Steps

To 6-bromo-3-fluoro-2-methylpyridine (2.0 g, 10.58 mmoles) in H2O (200 mL) was added potassium permanganate (1.67 g, 10.58 mmoles). The solution was heated at 100° C. for 16 hours at which time upon cooling 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 (2×200 mL), washed with NaCl(sat.), dried over MgSO4, filtered and concentrated to yield 6-bromo-3-fluoropicolinic acid (18%) as a white solid. LCMS (m/z): 221.9 (MH+); LC Rt=1.71 min.

Provenance & Evidence