Dimethyl Sulfoxide → 2',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)biphenyl-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

2-Bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzene (100 g), 3-formylphenylboronic acid (56 g), 10% palladium carbon 50% water-containing product (10 g) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4 g) were added to dimethyl sulfoxide (1000 mL). Tripotassium phosphate (132 g) dissolved in water (500 mL) was added, and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was left standing, an oil component was removed, and ethyl acetate was added. The insoluble material was removed by filtration, and washed with ethyl acetate. The filtrate was washed with 10% brine, and the organic layer was concentrated. Ethyl acetate was added, and the mixture was azeotropically distilled with dehydration. To the concentrate were added ethyl acetate and activated carbon (10 g), and the mixture was stirred at 45° C. The insoluble material was removed by filtration, and washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and isopropyl alcohol was added dropwise. The precipitated solid was collected by filtration, and the solid was washed with isopropyl alcohol, and dried under reduced pressure to give 2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (92.8 g).

Provenance & Evidence