Potassium Phosphate, Tribasic → HCID 23157405, compound

Participants

Reaction Steps

To a solution of methyl 3-(benzyloxy)-5-hydroxybenzoate (3.10 g, 12.0 mmol) and N-ethyldiisopropylamine (2.51 mL, 14.4 mmol) in dichloromethane (30 mL) was added dropwise trifluoromethanesulfonic anhydride (2.22 mL, 13.2 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in 1,2-dimethoxyethane (40 mL), and 2,6-dimethylphenylboronic acid (2.25 g, 15.0 mmol), tripotassium phosphate (3.82 g, 18.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.693 g, 0.600 mmol) were added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane) to give the title compound (3.60 g, yield 87%) as a yellow oil.

Provenance & Evidence