Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

Participants

Reaction Steps

Commercially available 4-bromobenzylalcohol (4.00 g, 21.5 mmol) was dissolved in DMF (100 mL), and tert-butyldimethylsilyl chloride (4.86 g, 32.2 mmol) and imidazole (2.20 g, 32.3 mmol) were added to the solution, followed by stirring at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:80) to obtain 4-bromobenzyloxy-tert-butyldimethylsilane (5.52 g, yield 85%).

Provenance & Evidence