Potassium Carbonate → 1-Bromo-4-(difluoromethoxy)-2-fluorobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-3-fluoro-phenol (962 mg, 5.037 mmol) in acetonitrile (25 mL) was added a solution of potassium carbonate (28.3 g, 181 mmol) dissolved in water (25 mL) all under nitrogen. To the reaction mixture was added 2-chloro-2,2-difluoroacetophenone (5 g, 25 mmol) and the reaction was heated to 80° C. for 4 hours. The reaction was cooled to room temperature and extracted with ethyl acetate (3×50 mL). The organic layer was dried with sodium sulfate, filtered and concentrated onto silica gel. Silica gel chromotography (5% ethyl acetate 95% heptane to 100% ethyl acetate over 55 minutes) furnished a clear oil (950 mg, 78%). LCMS m/z 531.7 (M−1) 1H NMR (400 MHz, METHANOL-d4) δ ppm 6.85 (s, 1 H) 6.92 (dd, J=8.88, 2.63 Hz, 1 H) 7.05 (t, 1 H) 7.38 (t, 1 H)

Provenance & Evidence