Hydrochloric Acid → 1-Bromo-5-fluoro-4-methoxy-2-methylbenzene

To a mixture of 4-bromo-2-fluoro-5-methylphenol (29.6 g, 144.2 mmol) and potassium carbonate (30.0 g, 218 mmol) in acetone (500 mL) was added iodomethane (69.0 g, 486 mmol). The resulting suspension was stirred at reflux for 4 hours. The reaction mixture was cooled to RT, poured into HCl (250 mL of 1 N solution) and extracted with ethyl acetate (3×250 mL). The combined organic layers were washed with sodium bicarbonate solution, dried over sodium sulfate and filtered. Evaporation of the solvent and purification on a silica column (5% ethyl acetate—hexanes) yielded 29.50 g (93%) of the title compound as a clear, colorless oil: 1H NMR (CDCl3): δ 2.33 (3H, s), 3.85 (3H, s), 6.82 (1H, d, J=8.79 Hz), 7.23 (1H, d, J=10.25 Hz); MS m/z,

1. temperatureat reflux for 4 hours
2. extractionextracted with ethyl acetate (3×250 mL)
3. washThe combined organic layers were washed with sodium bicarbonate solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customEvaporation of the solvent and purification on a silica column (5% ethyl acetate—hexanes)

ORD record

ord-dd8b765b81884086b62f295ebc44bd3a

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06723747B2