[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[O:20][C:21]([F:24])([F:23])[F:22])C>CCOCC>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][OH:9])=[C:14]([O:20][C:21]([F:22])([F:23])[F:24])[CH:15]=1A suspension of lithium aluminum hydride (834 mg, 22.0 mmol) in Et2O (20 mL) was cooled at 4° C. A solution of (E)-3-(4-bromo-2-trifluoromethoxy-phenyl)-acrylic acid ethyl ester (2.98 g, 8.79 mmol) in Et2O (9 mL) was added dropwise, and the mixture was stirred at ambient temperature for 90 min. The reaction was quenched with EtOAc (6 mL) and saturated aqueous NH4Cl was added dropwise. The aqueous layer was extracted with EtOAc (three times). The combined organic layer was washed with 1 M aqueous HCl, dried over MgSO4, filtered, concentrated, and purified by flash chromatography (silica gel, 25% EtOAc in hexane) to give 3-(4-bromo-2-trifluoromethoxy-phenyl)-propan-1-ol (1.14 g, 43%) as a colorless oil.
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