Imidazole → 4-Bromo-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-methoxybenzene

Participants

Reaction Steps

Imidazole (3.45 g) and t-butyldimethylchlorosilane (17.6 g) were added to a solution of 5-bromo-2-methoxybenzyl alcohol (10.0 g) in DMF (100 ml) under cooling with ice and the mixture was stirred for two hours. The reaction mixture was added to ice-cooled water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain [(5-bromo-2-methoxybenzyl)oxy](t-butyl)dimethylsilane (15.2 g).

Provenance & Evidence