Methanol → 6-Fluoro-4-oxo-3,4-dihydro-2H-1-benzopyran-2-carbonitrile

Participants

Reaction Steps

To a mixture of 72.2 g (0.44 mol) of 6-fluoro-4H-1-benzopyran-4-one obtained through the process as described in said Item b and 1.39 g (4.4 mmol) of zinc iodide in 610 ml of dry ether, 101 g (1.0 mol) of trimethylsilylcyanide were added under stirring. The mixture was heated at reflux temperature for 24 hours. After cooling the reaction mixture, the solution was poured into 500 ml of methanol, stirred for one hour at room temperature and evaporated in vacuo to dryness. Resulting residue was chromatographed on silica gel, eluting with dichloromethane to give 79.7 g (94.9%) of the desired compound.

Provenance & Evidence