Water → HCID 18782485, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 0.48 g, 12 mmol) was added to a stirred, cooled (0° C.) solution of N-(3-Bromo-4-methoxyphenyl)trifluoroacetamide (Description 43, 2.98 g, 10 mmol) in dimethylformamide (30 ml). The mixture was stirred at 0° C. for 30 min., then methyl iodide (0.75 ml, 1.70 g, 12 mmol) was added. The mixture was stirred at 0° C. for 30 min., then at room temperature for 3 h. Water (50 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic fractions were washed with water (4×50 ml) and brine (50 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane/CH2Cl2 (50:50 increasing to 30:70) to give the title compound as a colorless solid (2.72 g, 87%). 1H NMR (250 MHz, CDCl3) δ7.46 (1H, d, J 2.4 Hz), 7.18 (1H, dd, J 8.7, 2.4 Hz), 6.91 (1H, d, J 8.7 Hz), 3.94 (3H, s), and 3.32 (3H, s).

Provenance & Evidence