Sodium Carbonate → Methyl 6-fluoro-2'-hydroxy[1,1'-biphenyl]-3-carboxylate

Participants

Reaction Steps

To a solution of 2 g (8.45 mmol) of methyl-3-bromo-4-fluorobenzoate in 28 Ml of toluene at RT was added 0.49 g (0.42 mmol) of tetrakis(triphenyl phosphine)palladium(0), 1.95 g (8.9 mmol) of 2-(4,4,5,5,-tetramethyl-1.3.2-dioxaborolan-2-yl)phenol, 5.1 Ml (10.15 mmol) of 2M aqueous sodium carbonate solution and 14 Ml of n-propanol. The reaction mixture was heated at reflux for 18 h. The reaction mixture was cooled and diluted with ethyl acetate and water. The organic fraction was separated and washed with saturated NaCl solution (brine), dried over MgSO4, filtered and the filtrate was concentrated to an oil which was purified by chromatography (silica, 90:1, 30:1 successively CH2Cl2:acetone) to give the title compound. Mass Spectrum (ESI) m/e (M+1): 247.0.

Provenance & Evidence