Imidazole → Tert-butyl(2-fluoro-3-iodopropoxy)diphenylsilane

Participants

Reaction Steps

3-{[Tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropan-1-ol(2.03 g, 6.12 mmol) was dissolved in dichloromethane (20 ml). Iodine (4.66 g, 18.36 mmol), triphenyl phosphine (4.82 g, 18.36 mmol) and imidazole (1.25 g, 18.36 mmol) were added to the solution under cooling on ice and the mixture was stirred at room temperature for 23 hours. A saturated sodium thiosulfate aqueous solution was added to the reaction solution under cooling on ice and stirred for a while, the solution was extracted with dichloromethane and the extract was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 1.58 g (58%) of the title compound in the form of a yellowish solid.

Provenance & Evidence