Acetyl chloride → 1-[2-Methoxy-5-(pentafluoroethyl)phenyl]ethanone

Participants

Reaction Conditions

Reaction Steps

7.4 ml of BuLi at 2.5M in hexane are added, at −70° C., to a solution of 3.5 g of 1-methoxy-4-pentafluoroethylbenzene in 50 ml of anhydrous THF. The medium is stirred at −70° C. for 30 min and then at 0° C. for 45 min. 15.5 ml of a 1M solution of zinc chloride in ether are then added. After stirring at 0° C. for 10 min, 1.33 ml of acetyl chloride are added. The medium is then deoxygenated with nitrogen, and 332 mg of palladium benzyl(chloro)bis(triphenylphosphine) in 5 ml of anhydrous THF are introduced. The medium is stirred at 0° C. for 2 h 30 min and then at AT for 72 hours. The medium is run into a 2.5M HCl solution and then extracted in ether. The organic phase is washed with NaHCO3 at 5% in water, with water, and then with a saturated NaCl solution. After drying over MgSO4 and evaporation, the crude is purified by flash chromatography on silica, to give 2.25 g of a white solid.

Provenance & Evidence