4-Bromo-2,5-difluoronitrobenzene → 1-Bromo-2-fluoro-5-methoxy-4-nitrobenzene

Temperature

60 °C

1-Bromo-2,5-difluoro-4-nitrobenzene (15.0 g, 63.0 mmol) was added to a solution of sodium methoxide in methanol (164 mL, 0.5 M, Aldrich). The reaction was heated to 60° C. for 1 h. After cooling to room temperature, the solution was concentrated, and the residue was diluted with water (100 mL) followed by extraction with Ethyl acetate (2×80 mL). The organic phase was dried (Na2SO4) and concentrated to afford 5-bromo-4-fluoro-2-nitrophenyl methyl ether as an orange solid (15.2 g, 95% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.93 (s, 3 H), 7.76 (d, J=5.5 Hz, 1 H), 8.08 (d, J=8.4 Hz, 1 H).

1. temperatureAfter cooling to room temperature
2. concentrationthe solution was concentrated
3. additionthe residue was diluted with water (100 mL)
4. extractionfollowed by extraction with Ethyl acetate (2×80 mL)
5. dry with materialThe organic phase was dried (Na2SO4)
6. concentrationconcentrated

ORD record

ord-ddfcc2c7bb0c4cb2953b7296cb762564

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07981903B2