Imidazole → Silane, (4-bromophenoxy)(1,1-dimethylethyl)diphenyl-

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Reaction Steps

11.06 g (162.5 mmol) of imidazole in 30 ml of dimethylformamide are added dropwise at room temperature to 35.24 g (130.0 mmol) of tert-butylchlorodiphenylsilane and 11.25 g (65.0 mmol) of 4-bromophenol in 150 ml of dimethylformamide. After the reaction mixture has been stirred at room temperature for 1 hour, it is poured into 1000 ml of 5% strength aqueous sodium bicarbonate solution and extracted twice with 400 ml of dichloromethane, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness. Chromatographic purification (silica gel/hexane: ethyl acetate 8:2) gives 23.40 g of 4-bromophenyl tert-butyldiphenylsilyl ether. ##STR27##

Provenance & Evidence