Cesium carbonate → 3-{4-[3-(4-Chloro-2-phenoxy-phenoxy)-phenoxy]-2-methyl-phenyl}-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[4-(3-bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester (0.474 g, 1.36 mmol), 4-chloro-2-phenoxy-phenol (0.30 g, 1.36 mmol), cesium carbonate (0.531 g, 1.63 mmol), copper (I) chloride (0.067 g, 0.677 mmol) and 2,2,6,6-tetramethyl-3,5-heptanedione (0.063 g, 0.342 mmol) in 1-methyl-2-pyrrolidinone (5 mL) is heated to 120° C. for 20 hours under N2. The reaction is cooled and quenched with 1 N HCl (20 mL). The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 9/1 hexanes/ethyl acetate to afford 0.221 g (33%) of the title compound. Rf=0.29 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C29H25O5Cl 488, found 489 and 351 (M+1 and M+3, 100%).

Provenance & Evidence