Ethyl Acetate → HCID 68670137, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 32 mg (0.106 mmol) of 1-bromo-3-(isopropylsulfonyl)-5-(prop-1-en-2-yl)benzene, 11.2 mmol (0.0954 mmol) of Zn(CN)2 and 24.3 mg of (0.021 mmol) of Pd(PPh3)4 in 3 mL of DMF (degassed) was heated at 100° C. Over a period of 2.5 h, a total of 103 mg of Pd(PPh3)4 was added in 3 portions. Ethyl acetate and 10% NH4OH solution were added, and the organic layer was washed with H2O and brine. The aqueous layer was extracted with EtOAc (3×), and the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 28.6 mg of 3-(isopropylsulfonyl)-5-(prop-1-en-2-yl)benzonitrile as a yellow solid.

Provenance & Evidence