4-Bromophenol → HCID 59240083, compound

Participants

Reaction Steps

Into a 250 mL flask was weighed 570 mg (1.52 mmol) of 2-Bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-imidazole, 394 mg (2.25 mmol) of 4-bromophenol, 310 mg (2.25 mmol) of potassium carbonate, and 20 mL of acetonitrile. The flask was heated in an oil bath to reflux for 4 h. The crude reaction was washed into a separatory funnel with ethyl acetate and water. The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel flash chromatography by column chromatography eluting with MeOH-DCM (0:100 to 2:98) to afford 2-(4-Bromophenoxymethyl)-1-(2,6-dichloro-phenyl)-4-trifluoromethyl-1H-imidazole as an off white solid (417 mg, 59%); 1H NMR (400 MHz, CDCl3): δ 7.96 (d J=8.6 Hz 2H), 7.68 (d J=8.3 Hz 2H), 7.46 (m, 5H), 7.32 (m, 1H), 6.88 (d J=8.84 Hz 2H), 5.10 (s, 2H), 3.08 (s, 3H), MS (ES): 465 [M+H]+.

Provenance & Evidence