Imidazole → (4-Bromo-phenoxy)-triisopropylsilane

Participants

Reaction Steps

To a stirred solution of 4-bromophenol (25.1 g, 146 mmol), and imidazole (19.9 g, 292 mmol) in 1,2-dichloroethane (150 mL) at 23° C. was added triisopropylsilylchloride (34.4 mL, 161 mmol). The mixture was stirred for 12 h and poured onto saturated aqueous NH4Cl (400 mL), followed by extraction with CH2Cl2 (3×200 mL). The combined extracts were washed with brine (300 mL), dried (Na2SO4), and concentrated in vacuo to give a pale yellow oil which was crude oil was purified via short-path distillation (0.5 mmHg, 130° C.) to yield (4-Bromo-phenoxy)-triisopropylsilane as a colorless oil (53.0 g, 99% yield). Rf 0.81 (3:1 hexanes/EtOAc) IR (thin film) 2945, 2892, 2867 cm−1. 1H NMR (300 MHz, CDCl3) δ 7.30 (2H, d, J=9 Hz), 6.75 (2H, d, J=9 Hz), 1.29-1.18 (3H, m), 1.08 (18H, d, J=7 Hz). 13C NMR (75 MHz, CDCl3) δ 155.0, 132.0, 121.5, 112.9, 17.6, 12.4. HRMS calcd. for C15H26OSiBr (MH+) 329.0936, found 329.0937.

Provenance & Evidence