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 2-bromo-4-(trifluoroacetamido)anisole (Description 4(b); 2.98 g, 10 mmol) in dimethylformamide (30 ml). The mixture was stirred at 0° C. for 30 minutes, then methyl iodide (0.75 ml, 1.70 g, 12 mmol) was added. The mixture was stirred at 0° C. for 30 minutes, then at room temperature for 3 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with water (4×50 ml) then brine (50 ml), dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with hexane/CH2Cl2 (50:50 increasing to 30:70), to give the title compound as a colorless solid (2.72 g, 87%); δH (250MHz, CDCl3) 3.32 (3H, s, N--CH3), 3.94 (3H, s, ArOCH3), 6.91 (1H, d, J 8.7Hz, 6-H), 7.18 (1H, dd, J 8.7, 2.4Hz, 5-H), 7.46 (1H, d, J 2.4Hz, 3-H).

Provenance & Evidence