Water → (4-Bromo-2-methyl-benzyloxy)-trimethylsilane

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-bromo-2-methyl-phenyl)-methanol (Intermediate 133, 500.0 mg, 2.48 mmols), in 10 mL THF was added triethylamine (374.0 mg, 3.70 mmols) and chlorotrimethylsilane (297.0 mg, 2.70 mmols). The resulting solution was stirred for 17 hours at 25° C. and then treated with H2O and extracted with Et2O. The combined organic layers were washed with H2O, 10% aqueous HCl, saturated NaHCO3, and saturated NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound, 550.0 mg (81%), was isolated by column chromatography (5% EtOAc—hexanes) as a colorless oil.

Provenance & Evidence