Dimethyl Sulfoxide → 5-Bromo-2-[2-(3-methoxy-2-methyl-phenyl)-ethyl]-phenylacetonitrile

Participants

Reaction Conditions

Reaction Steps

To 5-bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenyliodomethane 9 (5.56 g; 12.5 mmol) in dichloromethane (10 mL), isopropyl alcohol (10 mL), and DMSO (3 mL), was added potassium cyanide (1.22 g; 18.8 mmol). The mixture was stirred at 42° C. for 16.5 hours and concentrated in vacuo. The resultant residue was taken up in dichloromethane and water. The solution was shaken and the layers were separated. The organic layer was washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to give an amber oil. The oil was chromatographed using SiO2 and hexane/ethyl acetate (3:2) as eluent to give compound 10, 1.99 g; 46% yield.

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