Sodium Carbonate → 4-(4'-Methoxy-biphenyl-4-yl)4-oxo-butyric acid, methyl ester

Participants

Reaction Steps

In a manner similar to Example 12, Step (b), (4-methoxyphenyl)boronic acid (0.913 g, 0.00601 mol) was allowed to react with 4-(4-bromo-phenyl)-4-oxo-butyric acid, methyl ester (1.356 g, 0.00500 mol) in the presence of tetrakis(triphenylphosphine)palladium(0) (0.173 g, 0.000150 mol) and 2.0 M aqueous sodium carbonate (5.0 mL, 0.010 mol) in toluene (10 mL) to give, after chromatography on silica gel (270 g, 230-400 mesh), eluting with dichloromethane (15×250 mL); dichloromethane-methanol (100:1, 19×225 mL; 50:1, 5×225 mL), 1.386 g of 4-(4′-methoxy-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid; mp 96.0-100.5° C.

Provenance & Evidence