Acetic Acid → 2-chloro-6-(trifluoroMethyl)pyridin-3-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 6-(trifluoromethyl)pyridine-3-ol (7 g, 40 mmol) and sodium carbonate (4.5 g, 4.2 mmol) in water (200 mL) was cooled in an ice bath. 0.7N Sodium hypochlorite solution (63.9 mL, 4.29 mmol) was added portionwise over 30 minutes, and the reaction stirred at 0° C. for 2 hours. The reaction mixture was acidified using acetic acid, and extracted into EtOAc (3×50 mL). The combined organics were washed with brine (2×50 mL), dried (MgSO4), filtered and concentrated. The product was purified by flash chromatography (0 to 25% EtOAc in hexanes) giving the title compound (1.6 g, 20%) as a solid. 1H NMR (400 MHz; CDCl3) δ 7.61 (1H, d), 7.45 (1H, d), 5.83 (1H, s).

Provenance & Evidence