Imidazole → 4-[2-(Tert-butyldimethylsilanyloxy)ethoxy]bromobenzene

Participants

Reaction Steps

To a solution of [2-(4-bromophenoxy)ethanol (10.0 g, 46 mmol) in 150 mL dry dimethylformamide (30 mL) was added t-butyldimethylsilyl chloride (8.34 g, 55 mmol) and imidazole (7.82 g, 115 mmol). Additional dimethylformamide (20 mL) was used to wash these materials into the reaction flask. The resulting solution was stirred overnight at room temperature with a Newman tube. It was poured onto water (200 mL) and extracted with ether (3×75 mL). The combined extracts were washed with 0.5 N HCl (200 mL), sat. NaHCO3 (200 mL), water (4×150 mL), and sat. NaCl (200 mL), dried over MgSO4, and filtered. The solvent was removed under reduced pressure on a rotary evaporator to give the crude product (16.5 g; >100%). 1H NMR (CDCl3) d 7.34 (2H, d, J=8.9), 6.78 (2H, d, J=8.9), 4.00-3.93 (4H, m), 0.89 (9H, s), 0.08 (6H, s). 13C NMR(CDCl3) d 158.1, 132.2, 116.4, 112.8, 69.6, 61.9, 25.9, 18.4. FDMS (m/e) 330 (M+, 79Br). It was used as 100% without purification.

Provenance & Evidence