Cesium carbonate → 2'-Fluoro-2-formyl-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-formyl-4-(trifluoromethyl-sulfonyloxy)benzoate (T29.2) (7.57 g, 24.2 mmol), 2-fluoro-5-methoxy-phenylboronic acid (commercially available from Aldrich) (12.4 g, 72.7 mmol), cesium carbonate (27.6 g, 84.9 mmol), and tetrakis(triphenylphosphine) palladium (2.80 g, 2.42 mmol) in 1,2-dimethoxyethane (DME) (75 mL) was degassed with N2 at room temperature The mixture was heated at 95° C. for 9 hours. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:19 EtOAc/hexane) and gave T29.3, a white solid, in 56% yield (2.9 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.88 (dd, J=4 Hz, 1H), 8.45 (s, 1H), 8.28 (m, 1H), 7.69 (d, j=8 Hz, 1H), 7.29 (t, J=9 HZ, 1H), 7.08 (m, 2H), 3.92 (s, 3H), 3.79 (s, 3H).

Provenance & Evidence