Bromocyclopropane → HCID 58392457, compound

Participants

Reaction Steps

A few drops of dibromoethane and then 6.30 g (52.1 mmol) of cyclopropyl bromide, dissolved in 20 ml of diethyl ether, were added under argon to 1.33 g (54.7 mmol) of magnesium in 90 ml of dry diethyl ether. The mixture was heated under reflux for 2 h. After cooling, 21 ml (9.94 mmol) of the supernatant reaction solution were added dropwise under argon to a solution of 850 mg (4.12 mmol) of 1-[2-fluoro-4-(trifluoromethyl)phenyl]ethanone in 17 ml of diethyl ether, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient with addition of 0.1% triethylamine) to result in 157 mg (15% of theory) of a mixture of the diastereomers of the title compound.

Provenance & Evidence