[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].CI.[C:15](=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(Cl)Cl>[Br:1][C:2]1[C:3]([O:12][CH3:15])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1A stirred solution of 30.0 g (0.127 mole) of 2-bromo-4-fluoro-5-nitrophenol, 26.9 g (0.19 mole) of methyl iodide, and 26.3 g (0.19 mole) of potassium carbonate in 200 mL of acetone was heated at reflux for five hours. The reaction mixture was filtered, and the filtrate concentrated under reduced pressure to give a residue. The residue was dissolved in methylene chloride and passed through a column of silica gel. The elute was concentrated under reduced pressure to give 30 g of 4-bromo-2-fluoro-5-methoxynitrobenzene; m.p. 74°-76° C.
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