Water → Methyl 3-methoxy-4-(4-methyl-3-thienyl)benzoate

Participants

Reaction Steps

Methyl 4-bromo-3-methoxybenzoate (Combi-Blocks, 2.50 g; 10.20 mmol) and 4-methyl-3-thiopheneboronic acid (1.59 g; 11.22 mmol), potassium carbonate (7.04 g; 51 mmol), tetrakis(triphenylphosphine)palladium(0) (1.17 g; 1.02 mmol) were mixed in toluene (10 mL) and water (10 mL) under N2 atmosphere. The reaction mixture was degassed with N2 for 10 min and was heated under reflux for 3 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with toluene. The filtrate was concentrated under vacuum to afford brown oil. It was taken in EtOAc and the organic layer was washed with a saturated aqueous solution of NaHCO3, water and brine. It was dried over MgSO4, filtered off and concentrated under vacuum giving a brown oil. LC/MS (Method A): 262.8 (M+1-1)+. HPLC (Method A) Rt 4.79 min (Purity: 63.0%).

Provenance & Evidence