Potassium Carbonate → 2-(4-Nitrophenyl)oxirane

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.

1. temperaturethe suspension cooled in an ice bath
2. customwas removed
3. stirringthe mixture stirred at room temperature for a further 16 hours
4. customThe methanol was evaporated
5. additionwater (50 mL) was added
6. extractionthe mixture extracted with DCM (3×100 mL)
7. washThe combined DCM phases were washed with brine
8. dry with materialdried (sodium sulfate)
9. customevaporated

ORD record

ord-61e3d530b6cc46dda75c29b11b6b52bd

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09421205B2