Cesium fluoride → HCID 68547678, compound

Participants

Reaction Steps

A mixture containing 4-bromo-5-bromomethylene-2(5H)-furanone (1 mmol), phenylboronic acid (2.2 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.05 mmol), tetrabutylammonium iodide (0.05 mmol) and cesium fluoride (3 mmol) in toluene (10 mL) and water (10 mL) were stirred for 48-72 h under nitrogen at room temperature. Brine (50 mL) was added and the product extracted with ethyl acetate (3×50 mL). The organic fractions were combined, washed with brine (3×50 mL), dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The resulting solid was chromatographed (silica gel: eluent 25:75 dichloromethane/light petroleum, 50:50 dichloromethane/light petroleum or 100% dichloromethane) giving the desired product—4-phenyl-5-bromomethylene-2-(5H)-furanone.

Provenance & Evidence