Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

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Reaction Steps

tert-Butyldimethylsilyl chloride (2.42 g, 16 mmol) was added to a mixture of (4-bromophenyl)methanol (2.0 g, 107 mmol) and imidazole (1.09 g, 16 mmol) in DMF (30 mL) and the resultant mixture was stirred at ambient temperature for 72 h. The mixture was concentrated to one third of the original volume then diluted with water (50 mL) and extracted with diethyl ether (3×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 0-5% diethyl ether in pentane) to afford the title compound as a colourless oil (3.21 g, 100%). 1H NMR (CDCl3, 400 MHz): 7.45-7.42 (m, 2H); 7.21-7.17 (m, 2H); 4.68 (s, 2H); 0.93 (s, 9H); 0.09 (s, 6H).

Provenance & Evidence