Imidazole → tert-Butyl(4-chloro-3-iodophenoxy)dimethylsilane

Participants

Reaction Steps

To a solution of 4-chloro-3-iodophenol (2 g. 7.86 mmol) in anhydrous 2-methyltetrahydrofuran (10 mL) was added tert-butyldimethylsilyl chloride (1.25 g, 8.28 mmol) followed by imidazole (642 mg, 68.1 mmol) The resulting mixture was stirred at room temperature for 3 hours. EtOAc (10 mL) was added and the mixture washed with aqueous sodium hydroxide solution (2M, 3×10 mL), water (10 mL), and brine (10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with heptane:EtOAc 90:10 to afford the title compound as colourless oil in 30% yield, 870 mg.

Provenance & Evidence