Water → Methyl 2-[4-(4-methoxyphenyl)phenyl]acetate

Participants

Reaction Steps

After a 1M aqueous sodium carbonate solution (2.8 ml) and tetrakis(triphenylphosphine)palladium (0) (116 mg, 0.10 mmol) were added to a solution of methyl (4-bromophenyl)acetate (573 mg, 2.50 mmol) obtained in Example (3-1) and 4-methoxyphenylboronic acid (380 mg, 2.50 mmol) in a mixture of toluene-ethanol (6:1, 6 ml), the mixture was heated under reflux for 4 hours. After the temperature of the reaction mixture was returned to room temperature, the mixture was poured into water and extracted with ethyl acetate three times. The organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a yellow solid. It was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=95/5-80/20) to give methyl (4′-methoxy-1,1′-biphenyl-4-yl)acetate as a pale yellow powder (617 mg, yield: 96%).

Provenance & Evidence