Hydrogen Bromide → 1-Bromo-3-fluoro-2-methoxybenzene

Temperature

50 °C

NaNO2 (12.0 g, 173 mmol, in 40 mL of water) solution was added dropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 mL of hydrobromic acid (47%) and 100 mL of water at −5˜0° C. and stirred for 1 hour. This solution was then added slowly to the suspension of CuBr (45.2 g, 315 mmol) in 50 mL of hydrobromic acid (47%) at 0° C. The resulting mixture was stirred at 0° C. for 1 hour then warmed to 50° C. and stirred for 1 hour. The reaction mixture was poured into ice water and extracted with ether (2×500 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to give 1-bromo-3-fluoro-2-methoxybenzene.

1. stirringThe resulting mixture was stirred at 0° C. for 1 hour
2. stirringstirred for 1 hour
3. extractionextracted with ether (2×500 mL)
4. washThe combined organic layer was washed with brine
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated

ORD record

ord-d32d5e49ba364cc691bd4f2d0a62c82b

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062070B2