Potassium Iodide → ((5-Bromo-2-iodobenzyl)oxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

A solution of 9.59 mmol (5-bromo-2-iodo-phenyl)-methanol [199786-58-8] in 10 ml of N,N-dimethylformamide is added at room temperature dropwise to a mixture of 11.5 mmol of sodium hydride (60% in paraffine) in 20 ml of N,N-dimethylformamide. The mixture is stirred for 1 h at room temperature. 10.6 mmol of tert-butyl-dimethylchloro silane and 1.00 mmol of potassium iodide are added and the mixture stirred for 30 minutes at room temperature. The reaction is quenched with water and extracted with toluene. The combined organics are washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as colourless oil. Rf=0.35 (dichloromethane); Rt=11.31 (gradient II).

Provenance & Evidence