Toluene → 4-(1,3-Thiazol-2-yl)benzaldehyde

Participants

Reaction Steps

2-Bromothiazole (0.538 ml, 6.06 mmol), 4-formylphenylboronic acid (1.0 g, 6.67 mmol), and Na2CO3 (1.61 g) were suspended in the mixed solution of toluene (25 ml), ethanol (5 ml), and H2O (5 ml). The mixture was stirred at room temperature for 15 minutes under an argon gas atmosphere. After reducing the pressure inside of the reaction container by using a vacuum line, the mixture was degassed by introducing Ar gas and this procedure was repeated twice. After that, tetrakis(triphenylphosphine)palladium (0.701 g, 0.606 mmol) was added, and the mixture was stirred for 15 hours by heating under reflux. The end point of the reaction was confirmed on TLC (EtOAc:n-hexane=1:4), and the mixture was cooled to room temperature. H2O (50 ml) and EtOAc (50 ml) were added and the mixture was stirred for 15 minutes. Black insoluble matter was removed by filtration with Celite and the filtrate was separated by the step of extraction/separation. The organic layer was washed with saturated brine (50 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified on silica gel column chromatography (EtOAc:hexane=1:3) to obtain the title compound (985 mg) as an opaque white solid.

Provenance & Evidence