Water → Methyl 2',4'-dimethoxy-2-methylbiphenyl-4-carboxylate

Participants

Reaction Steps

Methyl 4-bromo-3-methylbenzoate obtained in step 1 (3 g; 13.10 mmol), 2,4-dimethoxyphenylboronic acid (2.62 g; 14.4 mmol), potassium carbonate (9.05 g; 65.48 mmol), tetrakis(triphenylphosphine)palladium(0) (1.51 g; 1.31 mmol) were taken in toluene (15 mL) and water (15 mL) under N2 atmosphere. The reaction mixture was purged with vacuum and degassed with N2 and then refluxed for 6 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with toluene (200 mL). The filtrate was concentrated to afford a brown oil which was taken in EtOAc (300 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 solution (100 mL), water (100 mL) and brine (100 mL), dried over MgSO4 and concentrated affording the title compound as a brown oil that was used without further purification (3.7 g, 98%). HPLC (Method A) Rt 4.74 min (Purity: 59.9%).

Provenance & Evidence