Aluminium lithium hydride → 1-(4-Bromophenyl)-1H-imidazole-5-methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-bromophenyl)-3H-imidazole-4-carboxylic acid ethyl ester (4) (590 mg, 2.0 mmol) in dry THF was added lithium aluminium hydride (2.4 mL, 2.4 mmol, 1.0M in THF) dropwise at −40° C. under nitrogen, and the resulting mixture slowly warmed to −20° C. over 1 h. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution (3 mL) at −20° C. and diluted with ethyl acetate (40 mL). The suspension was filtered and the filtrate was washed with brine (20 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to afford [3-(4-bromophenyl)-3H-imidazol-4-yl]-methanol (5). MS (ES+): m/z 253/255 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=2.25 (br s, 1H), 4.56 (s, 2H), 7.14 (s, 1H), 7.40 (d, J=8.8 Hz, 2H), 7.63 (s, 1H), 7.64 (d, J=8.8 Hz, 2H).

Provenance & Evidence