Potassium Carbonate → 2-(4-Nitrophenyl)oxirane

Participants

Reaction Steps

2-Bromo-1-(4-nitrophenyl)ethanone (1.9 g, 7.9 mmol) was stirred in methanol (30 mL) and the suspension cooled in an ice bath. Sodium borohydride (0.33 g, 8.7 mmol) was added in one portion and after five minutes the ice bath was removed and the mixture stirred at room temperature. After three hours potassium carbonate (1.1 g, 7.9 mmol) was added, and the mixture stirred at room temperature for a further 16 hours. The methanol was evaporated, water (50 mL) was added, and the mixture extracted with DCM (3×100 mL). The combined DCM phases were washed with brine, dried (sodium sulfate) and evaporated to give the title compound (I83) (1.296 g, 99% yield) as a yellow solid; 1H NMR (400 MHz, CDCl3) δ 8.25-8.18 (m, 2H), 7.50-7.41 (m, 2H), 3.96 (dd, J=4.1, 2.5 Hz, 1H), 3.23 (dd, J=5.5, 4.1 Hz, 1H), 2.78 (dd, J=5.5, 2.5 Hz, 1H). LCMS Method C: rt 5.42 min.

Provenance & Evidence