Red-Al → HCID 178519947, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-(4-bromophenyl)-1H-imidazole-2-carboxylate (1.30 g, 4.40 mmol) in THF (30 mL) was slowly added Red-Al (65 wt % in toluene, 2.0 mL, 6.16 mmol) at −25° C. The reaction mixture was stirred for 4 h at the same temperature then slowly warmed to 0° C. over 1 h and quenched with 20% sodium tartrate solution (30 mL). The reaction was extracted with ethyl acetate (70 mL) and the organic layer was left for 3 h at room temperature. A solid separated and was collected by filtration, washed with ethyl acetate and dried to afford (4-(4-bromophenyl)-1H-imidazol-2-yl)methanol (778 mg, 71.0%). MS (EI) for C10H9BrN2O: 254.1 (MH+).

Provenance & Evidence