Sodium Carbonate → HCID 22326467, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of bromophenylacetic acid methyl ester (0.075 g, 0.328 mmol, 1.0 eq) in tetrahydrofuran (5.0 ml) was added 2-furanboronic acid (0.048 g, 0.426 mmol, 1.3 eq) and sodium carbonate (0.328 ml of a 2M soln in H2O). The solution was degassed and sonicated three times before adding tetrakis(triphenylphosphine)palladium (0.038 g, 0.033 mmol, 0.1 eq). The mixture was degassed and sonicated a further three times before stirring at 50° C. for 14 hours. After cooling to room temperature the solution was concentrated under reduced pressure. Column chromatography (silica, 20% EtOAc/hexane) yielded 3-furanylphenylacetic acid methyl ester (0.047 g, 67%) as a white solid; 1H-NMR (CDCl3, 400 MHz): δ 7.60 (1H, d, J=1.6 Hz), 7.47 (1H, t, J=1.0 Hz), 7.34 (1H, t, J=7.5 Hz), 7.19 (2H, m), 6.65 (1H, d, J=3.6 Hz), 6.48 (1H, dd, J=3.6, 1.6 Hz), 3.71 (3H, s), 3.66 (2H, s).

Provenance & Evidence