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

Participants

Reaction Steps

Methyl 4-bromo-3-(trifluoromethyl)benzoate (6 g; 21.20 mmol; 1 eq.), o-tolylboronic acid (3.17 g; 23.32 mmol; 1.10 eq.), potassium carbonate (14.65 g; 105.99 mmol; 5 eq.), tetrakis(triphenylphosphine)palladium(0) (2.45 g; 2.12 mmol; 0.10 eq.) 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 to afford 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