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

Participants

Reaction Steps

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,

Provenance & Evidence