Water → 1-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

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Reaction Steps

A solution 3-bromobenzyl alcohol (7.1 g, 38 mmol) and tert-butyldimethylsilyl chloride (5.7 g, 38 mmol) in N,N-dimethylformamide (40 mL) was stirred at room temperature for 5 h. Water (40 mL) was added and the mixture was extracted with hexanes. The combined extracts were washed with 10% aqueous hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride, and dried over magnesium sulfate. The desired product was isolated after concentration and purification by silica gel chromatography (hexanes). 1H NMR (CDCl3) 7.48 (s, 1H), 7.34 (m, 1H), 7.24 (m, 2H), 4.72 (s, 2H), 0.95 (s, 9H), 0.11 (s, 6H).

Provenance & Evidence