Methyl iodide → 2-Bromo-1-methoxy-4-(trifluoromethoxy)benzene

Participants

Reaction Steps

A mixture of 608 mg (2.4 mmol) of 2-bromo-4-trifluoromethoxyphenol, 0.35 mL (5.6 mmol) of iodomethane and 775 mg (5.6 mmol) of K2CO3 in 2 mL of DMF was stirred at rt for 2.5 h. The reaction mixture was partitioned between 100 mL of hexanes and 100 mL of H2O and the layers were separated. The organic layer was washed with 2×100 mL of H2O, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 25 g of silica gel using hexanes as the eluant afforded 579 mg (89%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 3.91 (s, 3H), 6.88 (d, J=9.2, 1H), 7.15-7.18 (m, 1H), 7.45 (app d, J=3.2, 1H).

Provenance & Evidence