BrBr.[OH-:3].[Na+].[Cl:5][C:6]1[C:11]([CH2:12][CH3:13])=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[C:15](=[O:17])C.O>O1CCOCC1>[Cl:5][C:6]1[C:11]([CH2:12][CH3:13])=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[C:15]([OH:17])=[O:3]Bromine (8.94 g) was added to an aqueous solution (35.6 mL) of sodium hydroxide (7.61 g) with stirring at 10° C., and a solution (37.4 mL) of 1-(2-chloro-3-ethyl-4-fluorophenyl)ethanone (3.74 g) in dioxane was added under ice-cooling (sodium chloride-ice bath). The mixture was warmed to room temperature and, after stirring for 1 hr, poured into water and partitioned with chloroform. The aqueous layer was adjusted to pH=3 with concentrated hydrochloric acid, and extracted with ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound as colorless crystals (yield: 3.33 g).
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