Chlorotrimethylsilane → (2-Bromo-4-(4-ethoxybenzyl)benzyloxy)trimethylsilane

Participants

Reaction Conditions

Reaction Steps

To a cooled solution (−10° C.) of (2-bromo-4-(4-ethoxybenzyl)phenyl)methanol (0.137 g, 0.43 mmol) and N-methylmorpholine (0.1 mL, 0.9 mmol) in 2 mL of THF under N2, was added dropwise trimethylsilyl chloride. One hour later, the reaction was allowed to stir at 35° C. for 5 h and then stirred at 20° C. overnight. After dilution with AcOEt, the mixture was cooled to 0° C. prior to cautiously adding H2O at a rate such that the temperature did not exceed 10° C. The organic layer was separated and washed with aqueous KH2PO4, H2O, and brine. The volatiles were removed using a rotary evaporator to yield the title compound, which was used in the next step without further purification.

Provenance & Evidence