Cesium fluoride → HCID 24825846, compound

Participants

Reaction Steps

A mixture containing (Z)-4-bromo-5-(bromomethylene)furan-2(5H)-one (0.503 g, 1.981 mmol), 2-thiopheneboronic acid (0.560 g, 4.377 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.072 g, 1.026×10−1 mmol), tetrabutylammonium iodide (0.072 g, 1.002×10−1 mmol) and cesium fluoride (1.257 g, 8.275 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-2-yl)-5-(thiophen-2-ylmethylene)furan-2(5H)-one 19.

Provenance & Evidence