Cesium carbonate → 4-(2',6'-Dimethoxyphenyl)-2-benzyloxy-benzoic acid, benzyl ester

Participants

Reaction Steps

A mixture of of 2-benzyloxy-4-chlorobenzoic acid, benzyl ester (1.0)g, 2.83 mmol), 2,6-dimethoxybenzene boronic acid (0.62 g, 3.4 mmol), Pd2dba3 (0.26 g, 0.28 mmol), Cs2CO3 (1.38 g, 4.2 mmol), and t-Bu3P (0.12 g, 0.57 mmol) was dissolved in 8.0 mL of THF and warmed to reflux for 24 h. The reaction mixture was cooled, diluted with Et2O and H2O and the layers were separated. The organic layer was successively washed with 1N HCl (2×100 ml), saturated NaHCO3 solution (2×50 ml), brine (1×50 ml), dried over anhydrous MgSO4 and concentrated. The residue was purified by flash column chromatography on silica gel eluted with a gradient of 25-50% Et2O in hexanes to give 4-(2′,6′-dimethoxyphenyl)-2-benzyloxy-benzoic acid, benzyl ester as a pale yellow oil.

Provenance & Evidence