Water → Methyl 2'-(methoxymethyl)-2-methylbiphenyl-4-carboxylate

Participants

Reaction Steps

Methyl 4-bromo-3-methylbenzoate (Aldrich 532878, 2 g; 8.73 mmol; 1 eq.), (2-methoxymethylphenyl)boronic acid (1.59 g; 9.60 mmol; 1.10 eq.), K2CO3 (6.03 g; 43.65 mmol; 5 eq.), tetrakis(triphenylphosphine)palladium (0) (1.01 g; 0.87 mmol; 0.10 eq.) were taken up in Toluene (10 mL) and water (10 mL) under N2 atmosphere. The reaction mixture was purged with vacuum, then degassed with N2 and then for 2 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with EtOAc (500 mL). The filtrate was concentrated to afford a yellow oil which was taken in EtOAc (100 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 solution (30 mL), water (30 mL) and brine (30 mL), dried over MgSO4 and concentrated affording the title compound as a brown oil used without further purification (3 g, quantitative). HPLC (Method A) Rt 5.20 min (Purity: 64.5%).

Provenance & Evidence