Hydrochloric Acid → 1-Chloro-4-[(2E)-2,3-difluoro-1-(2-methoxyethyl)-2-propenyl]benzene

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Reaction Steps

To a stirred solution of 1-chloro-4-[2,3,3-trifluoro-1-(2-methoxyethyl)-2-propenyl]benzene (2.25 g, 8.5 mmol) in tetrahydrofuran (56 ml) at −5° C. was added sodium bis(2-methoxyethoxy)aluminum hydride (RedAl, 6.7 ml of a 65% solution in toluene). The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to −5° C., and water (6.5 ml) was added dropwise with stirring, followed by 10% hydrochloric acid (30 ml). The resulting mixture was stirred for 45 minutes, diluted with water (50 ml) and extracted with methylene chloride (3×50 ml). The combined organic extracts were washed with water, saturated aqueous sodium bicarbonate, and water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound as a brown oil (1.92 g) which was characterized by IR, 1HNMR and mass spectral analysis and used without further purification.

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