Cesium fluoride → HCID 24825845, compound

Participants

Reaction Steps

A mixture containing (Z)-4-bromo-5-(bromomethylene)furan-2(5H)-one (0.502 g, 1.977 mmol), 3-thiopheneboronic acid (0.553 g, 4.322 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.068 g, 9.688×10−2 mmol), tetrabutylammonium iodide (0.037 g, 1.137×10−1 mmol) and cesium fluoride (1.221 g, 8.038 mmol) in toluene (10 mL) and water (10 mL) was stirred at room temperature for 72 h under nitrogen. Brine (50 mL) was added and the product extracted with ethyl acetate (3×50 mL). The organic fractions were combined, washed with brine (3×20 mL), dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to give a dark brown solid. The resulting solid was subjected to recrystallization to give (Z)-4-(thiophen-3-yl)-5-(thiophen-3-ylmethylene)furan-2(5H)-one 18.

Provenance & Evidence