Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

Participants

Reaction Steps

To a mixture of 4-bromobenzyl alcohol (18.0 g, 96.2 mmol) and imidazole (7.86 g, 115 mmol) in N,N-dimethylformamide (200 ml) was added tert-butyl dimethylchlorosilane (17.4 g, 115 mmol) at room temperature. The mixture was stirred for 5 hours. The mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=95/5) to afford (4-bromobenzyloxy) (tert-butyl)dimethylsilane as a colorless oil (27.7 g, 91.8 mmol, 92%).

Provenance & Evidence