Tetrahydrofuran → 4-Bromo-2-methoxy-6-methylbenzaldehyde

Participants

Reaction Steps

To a solution of 4-bromo-2-methoxy-6-methyl-benzonitrile (2.8 g, 12.38 mmol) in tetrahydrofuran (24.8 ml) is added diisobutylaluminium hydride (1.2 M in toluene) (24.8 ml, 29.7 mmol) at −78° C. The reaction mixture is slowly warmed to RT and stirred at RT for 18 h. The reaction is quenched with 1 M hydrochloric acid at 0° C. The resulting mixture is stirred at RT for 1 h and extracted with ethyl acetate (3×50 ml). The combined organic layers are washed with water (40 ml), dried over sodium sulfate and evaporated. The crude product is purified by column chromatography (silica gel, 1.5% ethyl acetate/hexane) yielding 4-bromo-2-methoxy-6-methyl-benzaldehyde (1.25 g, 5.45 mmol, 44%).

Provenance & Evidence