Water → Methyl 2'-methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

Participants

Reaction Steps

Methyl 4-bromo-3-(trifluoromethyl)benzoate (6.0 g, 21.2 mmol), o-tolylboronic acid (3.17 g, 23.3 mmol), potassium carbonate (14.7 g, 106.0 mmol), tetrakis(triphenylphosphine)palladium(0) (2.45 g, 2.12 mmol) were taken up in toluene (30 mL) and water (30 mL) under N2 atmosphere. The reaction mixture was refluxed for 3 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and rinsed with toluene (200 mL). The filtrate was concentrated to afford a brown oil which was taken up in EtOAc (200 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (50 mL), water (50 mL) and brine (50 mL), dried over MgSO4 and concentrated affording the title compound as a brown oil (6.4 g, quantitative). HPLC (Method A) Rt 5.33 min (Purity: 60%).

Provenance & Evidence