C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][OH:11].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.[Cl-].[NH4+]>CN(C)C=O.O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:8][CH2:9][CH2:10][OH:11])=[CH:15][CH:14]=1Potassium carbonate (12.0 g) and 3-bromo-1-propanol (5.1 mL) were added to a solution of 4-bromophenol (5.0 g) in N,N-dimethylformamide (200 mL) under ice-cooling, and the mixture was stirred at room temperature for 8.5 hours. The reaction solution was ice-cooled and a saturated ammonium chloride solution and water were added, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1→4:1→3:1) to give 3-(4-bromophenoxy)propan-1-ol as a crude product.
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