2,2,2-Trifluoro-4'-methoxyacetophenone → 2,2,2-Trifluoro-1-(4-hydroxyphenyl)ethanone

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Reaction Steps

2,2,2-Trifluoro-1-(4-methoxy-phenyl)-ethanone (5 g, 25 mmol) was added to a solution of lithium chloride (3 g, 71 mmol) in DMF (84 mL). After the reaction mixture was refluxed for 5 days, it was cooled to room temperature and then quenched with 200 mL 1M HCl. The mixture thus formed was extracted with diethyl ether (3×100 mL). The combined organic phases were washed with H2O (3×300 mL), followed by brine (1×200 mL) and then dried over Na2SO4. The organic phase was collected by filtration and concentrated by rotary evaporation to yield yellow oil. The crude material was purified by flash column chromatography (0-25% ethyl acetate/hexanes) to yield intermediate compound (1) as a beige solid (4.1 g, 88%). 1H NMR (400 MHz, DMSO-D6): δ 11.14 (s, 1H), 7.94 (m, 2H), 6.98 (m, 2H); 19F NMR (376 MHz, CDCl3): δ −70.4.

Provenance & Evidence