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

Participants

Reaction Conditions

Reaction Steps

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

Provenance & Evidence