Imidazole → [(4-Bromo-2-thienyl)methoxy]t-butyldimethylsilane

Participants

Reaction Steps

To a solution of (4-bromo-thiophen-2-yl)-methanol (25 g, 130 mmol) in dichloromethane was added imidazole (9.7 g, 142 mmol) followed by tert-butyldimethylsilyl chloride (23.4 g, 156 mmol). The white suspension was stirred at room temperature for 30 minutes. The insoluble was filtered off. The filtrate was concentrated. The residual oil was chromatographed through silica gel (n-heptane/dichloromethane, 90/10 as eluant) to produce (4-bromo-thiophen-2-ylmethoxy)-tert-butyl-dimethyl-silane [34.6 g, Intermediate (67)] as a yellowish oil. LC/MS: 307.0 (M+H), RT=4.38 minutes.

Provenance & Evidence