Potassium Carbonate → Methyl 4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoate

Participants

Reaction Steps

Methyl 4-bromo-3-(trifluoromethyl)benzoate (Intermediate 19, step 1) (3.50 g; 12.37 mmol; 1 eq.), 4-methyl-3-thiopheneboronic acid (1.93 g; 13.60 mmol; 1.10 eq.), potassium carbonate (8.54 g; 61.83 mmol; 5 eq.), tetrakis(triphenylphosphine)palladium(0) (1.43 g; 1.24 mmol; 0.10 eq.) were taken up in Toluene (17.50 mL) and water (17.50 mL) under N2 atmosphere. The reaction mixture was purged with vacuum, then degassed with N2 for 5 minutes and then refluxed for 24 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 that was taken in EtOAc (300 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 solution (100 mL), water (100 mL) and brine (100 mL), dried over MgSO4 and concentrated affording the title compound as a brown oil (3.7 g, 99%). HPLC (Method A) Rt 5.21 min (Purity: 68.1%).

Provenance & Evidence