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

Participants

Reaction Steps

Methyl 4-bromo-3-(trifluoromethyl)benzoate (6 g; 21 mmol), o-tolylboronic acid (3.2 g; 23 mmol), potassium carbonate (14.7 g; 106 mmol), tetrakis(triphenylphosphine)palladium(0) (2.5 g; 2.12 mmol) were taken up in toluene (30 mL) and water (30 mL) under N2 atmosphere. The reaction mixture was purged with vacuum for 5 minutes, then degassed with N2 and then refluxed for 3 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with toluene (200 mL). The filtrate was concentrated, affording a brown oil which was taken in EtOAc (200 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 solution (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: 60.0%).

Provenance & Evidence