Triisopropylsilyl chloride → (5-Bromo-2-chlorobenzyloxy)triisopropylsilane

Participants

Reaction Steps

To a solution of 5-bromo-2-chlorobenzyl alcohol (425 mmol) in DMF (400 mL) was added imidazle (58 g, 850 mmol), 4-(dimethylamino)pyridine (2.6 g, 21 mmol), and triisopropylsilyl chloride (136 mL, 638 mmol). The resulting solution was stirred at ambient temperature for 15 h, diluted with a saturated ammonium chloride and extracted with EtOAc. The organic layer was washed with water then brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to yield the titled compound 32 (152 g, 403 mmol, 95%) as a colorless oil.

Provenance & Evidence