Cesium carbonate → 3-[4-(3-Bromo-5-methyl-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

The mixture of 1,3-dibromo-5-methyl-benzene (15 g, 0.06 mol), 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (3.9 g, 0.02 mol), CuCl (1 g, 0.01 mol), 2,2,6,6-tetramethyl-heptane-3,5-dione (0.92 g, 0.005 mol) and Cs2CO3 (7.8 g, 0.024 mol) in 40 mL of dry NMP is heated to 120° C. for overnight. The mixture is cooled to rt and diluted with Et2O and filtered through a pad of celite. Organic layer is washed with 1N HCl, H2O and brine, and then dried over Na2SO4, filtered and concentrated. Crude material is purified by chromatography (hexanes/acetone=20:1) to afford the title compound (59%) as a yellow oil. Rf=0.29 (20/1 hexanes/acetone). 1H NMR (400 MHz, CDCl3).

Provenance & Evidence