Ethyl Acetate → 2',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)(1,1'-biphenyl)-3-methanol

Participants

Reaction Steps

2-Bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzene (1.0 g), 3-hydroxymethylphenylboronic acid (0.497 g, 1.05 eq), triphenylphosphine (65.3 mg, 0.08 eq) and tetrabutylammonium bromide (50.2 mg, 0.05 eq) were dissolved in tetrahydrofuran (12 mL). Tripotassium phosphate (1.98 g, 3 eq) dissolved in water (5 mL) was added, and palladium acetate (14.0 mg) was added under a nitrogen atmosphere. The mixture was stirred under heated reflux for 8 hr. To the reaction mixture was added ethyl acetate (12 mL), and the insoluble material was removed. The filtrate was partitioned, and the organic layer was washed with 10% brine. After treatment with activated carbon, ethanol was added, and the mixture was concentrated is under reduced pressure. To the obtained oil was added ethyl acetate (3 mL), and the oil was dissolved. n-Heptane (10 mL) was added to allow crystallization. The obtained crystals were collected by filtration, and dried to give the title compound (0.893 g).

Provenance & Evidence