Water → Methyl 2'-methoxy-2-methylbiphenyl-4-carboxylate

Participants

Reaction Steps

Methyl 4-bromo-3-methylbenzoate (ABCR, 4.90 g; 21.39 mmol; 1 eq.), 2-methoxyphenylboronic acid (3.575 g; 23.53 mmol; 1.10 eq.), potassium carbonate (14.781 mg; 107 mmol; 5 eq.), tetrakis(triphenylphosphine)palladium(0) (2.5 mg; 2.14 mmol; 0.10 eq.) were mixed in toluene (24.5 mL) and water (24.5 mL) under N2 atmosphere. The reaction mixture was degassed with N2 for 10 min and was heated under reflux for 6 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with toluene (500 mL). The filtrate was concentrated under vacuum to afford brown oil. It was taken in EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL) and brine (200 mL). It was dried over MgSO4, filtered off and concentrated under vacuum giving a brown oil. It was purified by flash chromatography (cHex/EtOAc 9:1), affording the title compound as a colorless oil (4.38 g, 80%). 1H NMR: (DMSO-d6, 300 MHz) δ 7.94 (s, 1H), 7.89-7.86 (dd, J=8.06 Hz, J=1.61 Hz, 1H), 7.51-7.46 (m, 1H), 7.34-7.31 (d, J=8.13 Hz, 1H), 7.21-7.09 (m, 3H), 3.95 (s, 3H), 3.79 (s, 3H), 2.19 (s, 3H). LC/MS (Method A): 257.0 (M+H)+. HPLC (Method A) Rt 4.85 min (Purity: 98.9%).

Provenance & Evidence