Hydrochloric Acid → 3-{4-[5-(2-Bromo-4-trifluoromethyl-phenoxy)-2-methyl-phenoxy]-2-methyl-phenyl}-propionic acid ethyl ester

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Reaction Conditions

Reaction Steps

A mixture of 3-[4-(5-hydroxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (Example 84, Step D) (0.46 g, 1.46 mmol), 3-bromo-4-fluorobenzotrifluoride (0.35 g, 1.45 mmol) and 325 mesh potassium carbonate (0.21 g, 1.52 mmol) in dry DMSO (10 mL) is heated to 100° C. and stirred for 6 hours under N2. The reaction is cooled and acidified with 1 N HCl. 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 0.633 g (81%) of the title compound. Rf=0.38 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C26H24O4F3Br 536, found 554 and 556 (M+NH4, 100%).

Provenance & Evidence