Imidazole → (3-Bromo-2-methylphenethoxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

A solution of 2-(3-bromo-2-methylphenyl)ethanol [Aromatic Intermediate 22, step b] (1.67 g) and imidazole (1.60 g) in DMF (20 mL) was cooled in ice-water, treated with tert-butyldimethylchlorosilane (1.31 g), then removed from the cooling bath and stirred at room temperature overnight. The solution was poured into water and extracted twice with diethyl ether. The combined organic extracts were washed twice with water, once with brine, then dried over anhydrous magnesium sulphate and purified by flash chromatography on silica eluted with 10% dichloromethane in isohexane to afford the subtitled compound as a colourless oil. Yield 2.06 g.

Provenance & Evidence