C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9]Br.[C:11]([C:15]1[CH:16]=[C:17]([C:25](=[O:27])[CH3:26])[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[C:20]=1[OH:21])([CH3:14])([CH3:13])[CH3:12].C(OCC)(=O)C>CN(C)C=O>[Br:7][CH2:8][CH2:9][O:21][C:20]1[C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]([C:25](=[O:27])[CH3:26])=[CH:16][C:15]=1[C:11]([CH3:14])([CH3:13])[CH3:12]Potassium carbonate (4.65 g, 33.7 mmol) and 1,2-dibromoethane (31.7 g, 166.6 mmol) were added to a solution of 1-[3-(tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone (8.0 g, 33.7 mmol) in dimethylformamide (200 ml) and the mixture was stirred at room temperature for 12 hours. Ethyl acetate was added, the reaction mixture was washed with water and brine in that order and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield 1-[4-(2-bromoethoxy)-3-(tert-butyl)-5-nitrophenyl]-1-ethanone (8.1 g).
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