Hydrochloric Acid → HCID 67202260, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of ZnCl2 (0.390 g, 2.85 mmol) in 5 ml of dry THF at T=0° C. under nitrogen atmosphere commercial isopropylmagnesium chloride (2M in Et2O, 2.85 mL, 5.70 mmol) was added. After stirring 20 min the catalyst (dppf)PdCl2 (1%, 0.057 mmol) was added and, then, a solution of 2-(chlorocarbonyl)phenylpropionitrile (5.72 mmol), prepared as above described, in dry THF (5 mL) was added dropwise. The mixture was stirred 1 h at 0° C. then 3 h at room temperature. After cooling to 0° C., 3N HCl (10 mL) and Et2O (30 ml) were added. The aqueous layer was separated and the organic layer washed sequentially with a saturated solution of NaHCO3 (2×30 mL) and brine (30 mL). After drying on Na2SO4 and solvent evaporation under reduced pressure a residue was obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 95:5), afforded 2-[3-(isobutyryl)phenyl]propionitrile as pale yellow oil (0.804 g, 4.64 mmol). Yield 81%.

Provenance & Evidence