Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

Participants

Reaction Steps

To a solution of p-bromobenzyl alcohol (5.0 g, 26.7 mmol) in DMF (10 mL) was added imidazole (4.54 g, 66.7 mmol) followed by addition of tert-butyldimethylsilyl chloride (6.01 g, 40 mmol). The progress of the reaction was monitored by TLC. When the reaction was complete (about 2 h), methanol was added and diluted by 20% ethyl acetate in hexane. The organic layer was washed several times with water and then with brine, dried, concentrated under reduced pressure to give 7.5 g of the crude product which was passed through a short column chromatography to give 7.3 g (91%) of the desired compound.

Provenance & Evidence