Sodium Carbonate → 5-[3,5-bis(trifluoromethyl)phenyl]furan-2-carbaldehyde

Participants

Reaction Steps

A solution of 5-bromofuran-2-carbaldehyde (2.54 g, 14.5 mmol), [3,5-bis(trifluoromethyl)phenyl]boronic acid (3.93 g, 15.2 mmol), tetrakis(triphenylphosphine)palladium (0.59 g, 0.51 mmol) and 2M sodium carbonate solution (36 mL, 72 mmol) in THF (150 ml) was stirred under an argon atmosphere for 16 hr. The reaction solution was allowed to cool to room temperature and concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate filtration, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate), and the obtained solid was disrupted in hexane to give the title compound (4.46 g, yield>99%) as a pale-yellow solid. LC/MS (ESI+) m/z: 309 (M+H)+.

Provenance & Evidence