Dimethylformamide → 7-(4,4,4-Trifluoro-1,1-dimethyl-3-oxobutyl)-2,3-dihydrobenzofuran-5-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of 201 mg (0.57 mmol) of the above 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one, 144 mg (1.22 mmol) of zinc cyanide and 24 mg (0.021 mmol) of tetrakis(triphenylphosphine)palladium(0) in 2 mL of DMF was warmed at 130° C. After 36 hours, the mixture was cooled, diluted with 10 mL of saturated aqueous ammonium chloride, and extracted with three 7 mL portions EtOAc. The combined organic layers were washed with three 7 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was adsorbed onto silica gel and chromatographed on silica gel using EtOAc-hexanes (0:100, then 1:99, then 2:98, then 3:97, then 4:96) to afford 102 mg (60%) of 7-(4,4,4-trifluoro-1,1-dimethyl-3-oxobutyl)-2,3-dihydrobenzofuran-5-carbonitrile as a white solid.

Provenance & Evidence