Ammonium Chloride → 2-[4-(Trifluoromethyl)benzoyl]cyclopropanecarbonitrile

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Reaction Steps

Under argon, a few drops of dibromoethane and a solution of 4.00 g (14.7 mmol) of 1-iodo-4-(trifluoromethyl)benzene in 10 ml of dry diethyl ether were added to 375 mg (15.4 mmol) of magnesium in 40 ml of dry diethyl ether, and the mixture was heated under reflux for 2 h. After cooling, the supernatant reaction solution was added dropwise under argon to 2.00 g (13.0 mmol) of the compound from Example 73A in 50 ml of THF, and the mixture was stirred at RT overnight. The reaction solution was then added to saturated aqueous ammonium chloride solution, the phases were separated, and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. Purification of the residue by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) resulted in 1.42 g (46% of theory) of the title compound.

Provenance & Evidence