Sodium Carbonate → Ethyl 2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carboxylate

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To a mixture of ethyl 5-bromo-2-ethylthiophene-3-carboxylate (4.61 g) synthesized above, 4-(trifluoromethyl)phenylboronic acid (5.00 g), sodium carbonate (3.71 g), water (20 mL) and N,N-dimethylformamide (100 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II).dichloromethane adduct (1.43 g). The reaction mixture was deaerated, and stirred under an argon atmosphere at 80° C. for 2 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio) to give the title compound (5.18 g, 90%) as a white solid.

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