Cesium carbonate → Methyl 2-(4-(benzyloxy)-3,5-dichlorophenylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (5.98 g, 19 mmol) was added to a stirring solution of 4-(benzyloxy)-3,5-dichloroaniline (5.27 g [crude from previous step], 19 mmol) in toluene. Rac-BINAP (0.6 g, 7.5 mol %) and methyl 2-bromobenzoate (1.84 ml 13 mmol,) were added. Palladium(II) acetate (0.147 g, 5 mol %) was added and the mixture heated to 100° C. After 12 h the mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with pH 7 buffer solution (50 mL) and extracted with ethyl acetate (100 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to afford a residue that was purified by column chromatography (3:1, petroleum ether/dichloromethane) to afford methyl 2-(4-(benzyloxy)-3,5-dichlorophenylamino)benzoate as a white solid (94% yield).

Provenance & Evidence