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

Participants

Reaction Steps

To a solution of 2.17 g (10.0 mmol) of 5-bromo-2-methoxybenzyl alcohol in 10 mL of N,N-dimethylformamide was added 1.36 g (20.0 mmol) of imidazole, then 2.26 g (15.0 mmol) of tert-butyldimethylsilyl chloride. The reaction was stirred at ambient temperature for 30 min, and poured into 100 mL of water. The aqueous suspension was extracted with diethyl ether (3×15 mL), then the combined ether layers were back extracted with 1 M HCl (2×15 mL), saturated NaHCO3(aq.) (2×15 mL), and brine (1×15 mL), dried over MgSO4, filtered, and concentrated to an oil. This was purified via silica gel chromatography, eluting with 95:5 hexanes:ethyl acetate to give 2.91 g (88%) of the titled compound as a colorless oil.

Provenance & Evidence