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

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a mixture of palladium chloride (82.8 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (387.7 mg), N,N-dimethylacetamide (500 mL) and diisopropylethylamine (60.4 g) was stirred at 70° C. for 2 hr. To the obtained mixture were added 2-bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzene (100.0 g) and 3-formylphenylboronic acid (46.7 g), and the mixture was stirred at 70° C. for 1 hr. Deaerated water (450 mL) was added dropwise at 70° C., and the mixture was stirred for 8 hr. The reaction mixture was cooled, 10% brine (200 mL) was added, and the mixture was extracted with toluene (600 mL). The aqueous layer was extracted again with toluene (600 mL). The organic layers were combined, and washed with 10% brine (600 mL) and then water (600 mL). To the organic layer was added activated carbon (10.0 g), and the mixture was stirred at room temperature for 30 min. The insoluble material was removed by filtration, and washed with toluene (300 mL). The filtrate was concentrated to 300 mL under reduced pressure, to which was added toluene (600 mL), and the mixture was concentrated again to 300 mL. To the concentrated solution was added ethanol (300 mL), and the mixture was stirred at room temperature for 30 min. Normal heptane (1200 mL) was added dropwise, and the mixture was stirred at room temperature for 1 hr and at 5° C. for 2 hr. The precipitated solid was collected by filtration, and the solid was washed with a mixture (300 mL) of ethanol*normal heptane (1:4), and dried under reduced pressure to give 2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (96.0 g).

Provenance & Evidence