Trimethylsilyl cyanide → HCID 53403951, compound

Participants

Reaction Steps

To a solution of 2.5 g (10.73 mmol) of 2-bromo-1-(2-fluoro-4-hydroxyphenyl)ethanone in 100 ml of acetonitrile are respectively added 1.2 g (11.8 mmol) of trimethylsilyl cyanide and 12.3 ml (12.3 mmol) of tetrabutyl-ammonium fluoride solution (1M in THF). The reaction mixture is stirred at room temperature for 16 h then diluted with an aqueous solution saturated with sodium chloride. The product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered, then evaporated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 5:5) to give 1.2 g (62%) of 3-(2-fluoro-4-hydroxyphenyl)-3-oxopropanenitrile in the form of a yellow solid.

Provenance & Evidence