Hydrochloric Acid → 3-Chloro-1-(3-chlorophenyl)-1-propanone

Participants

Reaction Steps

To a solution of zinc chloride (0.5 M in THF, 20.40 mL, 10.20 mmol) was added a solution of (3-chlorophenyl) magnesium bromide (0.5 M in THF, 20.00 mL, 10 mmol) and the mixture was stirred at ambient temperature for 20 min. Pd(PPh3)4 (578 mg, 0.500 mmol) was added to the above mixture and the reaction was then cooled to 0° C. A solution of 3-chloropropanoyl chloride (1.008 mL, 10.50 mmol) in THF (anhydrous) (10 mL) was added and the reaction was stirred at 0° C. for 2 h. After this time, the mixture was acidified with 3 N HCl and extracted with Et2O (3×). The combined organic layer was washed with saturated aqueous NaHCO3, brine, dried (Na2SO4), filtered and evaporated to an oil which was purified using silica gel chromatography to give the desired product (635 mg, 31%). MS (ESI) m/z: 202.9 (M+H)+.

Provenance & Evidence