[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:15]OS(=O)(=O)OC.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([O:11][CH3:15])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1
A mixture of the 1-(5-bromo-2-hydroxy-3-nitrophenyl)-1-ethanone (17.4 g), dimethylsulfuric acid (12.7 g), potassium carbonate (13.8 g) and acetone (200 mL) was heated to reflux for 15 hours, and then water was added to the mixture and extraction was performed with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (16.2 g) as a yellow oil.
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