Cesium carbonate → HCID 69071885, compound

Participants

Reaction Conditions

Reaction Steps

Intermediates 3-methyl-5-(2-phenoxy-4-trifluoromethyl-phenoxy)-phenol (0.49 g, 1.36 mmol) and (4-bromo-2-methyl-phenoxy)-acetic acid ethyl ester (0.37 g, 1.36 mol) were combined with cesium carbonate (0.53 g, 1.63 mol), and 2,2,6,6-tetramethyl-3,5-heptanedione (0.063 g, 0.342 mmol) in 1-methyl-2-pyrrolidinone (10 mL) is purged with N2, and then copper (I) chloride (0.067 g, 0.677 mmol) is added. The reaction mixture is heated to 120° C. for 20 hours under N2. The mixture is diluted with water and extracted with Et2O. 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 0.094 g (13%) {2-methyl-4-[3-methyl-5-(2-phenoxy-4-trifluoromethyl-phenoxy)-phenoxy]-phenoxy}-acetic acid ethyl ester that was saponified with ethanol and 5 N NaOH to afford 0.072 g (81%) 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calcd for C29H23O6F3 524, found 525 (M+1, 100%).

Provenance & Evidence