Imidazole → 3-(t-Butyldimethylsiloxy)iodobenzene

Participants

Reaction Conditions

Reaction Steps

3-Iodophenol (110 g, 0.50 mol, 1 eq) and imidazole (93.6 g, 1.375 mol, 2.75 eq) were placed in a 2000 ml flask with dichloromethane (1150 mL) and cooled in an ice water bath to 15° C. under nitrogen. tert-Butyldimethylchlorosilane (82.9 g, 0.55 mol, 1.1 eq) in dichloromethane (200 mL) was added dropwise through an addition funnel and the reaction mixture was stirred overnight. The reaction solution was washed with 0.5 N sodium hydroxide solution (3×200 mL), water (3×200 mL) and brine (200 ml) and dried over sodium sulfate. The solvent was removed under reduced pressure leaving 166.34 g of crude (3-iodo-phenoxy)-tert-butyl-dimethyl-silane. 1H NMR (300 MHz, CDCl3) δ 7.27 (ddd, J=8.0, 2.0, 1.0 Hz), 7.19 (dd, 1H, J=2.0, 2.0 Hz), 6.92 (dd, 1H, J=8.0, 8.0 Hz), 6.77 (ddd, 1H, J=8.0, 2.0, 1.0 Hz).

Provenance & Evidence