Tetrahydrofuran → HCID 11287711, compound

Participants

Reaction Steps

Into a 200-mL eggplant type flask were introduced 6.45 g (34.9 mmol) of 2-bromobenzaldehyde, 5.0 g (29.1 mmol) of 1-naphthylboronic acid, 0.15 g of tetrakis(triphenylphosphine)palladium, 60 mL of tetrahydrofuran, 10 g (73 mmol) of potassium carbonate, and 20 mL of water. This reaction mixture was heated with refluxing overnight. After washing with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution and drying with anhydrous magnesium sulfate, the extract was concentrated to obtain yellow crystals. These crystals were purified by silica gel chromatography (solvent: hexane/toluene) to obtain 5.4 g of 2-(1-naphthyl)benzaldehyde (yield, 81%).

Provenance & Evidence