Water → 4'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

4-Bromo-3,5-dimethylphenol (10.1 g, 50.0 mmol) and (3-formylphenyl)boronic acid (8.25 g, 55.0 mmol) were dissolved in a mixed solution of 1 M aqueous sodium carbonate solution (150 mL), ethanol (50 mL) and toluene (150 mL), and after argon substitution, tetrakis(triphenylphosphine)palladium(0) (2.89 g, 2.50 mmol) was added. The reaction mixture was stirred at 80° C. for 27 hr under argon atmosphere. After cooling the reaction mixture, water and ethyl acetate were added, and the insoluble material was filtered off through celite. The filtrate was separated into an aqueous layer and an organic layer, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-40:60), and recrystallized from ethyl acetate-hexane to give the title compound (8.53 g, yield 74%) as colorless prisms.

Provenance & Evidence