[CH3:1][O:2]/[N:3]=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])/[C:5]([NH:7][CH3:8])=[O:6].C1C(=O)N([Br:23])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1/[C:4](=[N:3]\[O:2][CH3:1])/[C:5]([NH:7][CH3:8])=[O:6]To (E)-2-methoxyimino-2-(2-methylphenyl)-N-methylacetamide (2.66 g, 0.01 mol), added were carbon tetrachloride (20 ml), NBS (1.96 g, 0.011 mol) and α,α'-azobis(isobutyronitrile) (0.16 g, 0.001 mol), and the reaction mixture was heated under reflux for 1 hour. After completion of the reaction, undissolved materials were removed and the remaining mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/toluene) to give (E)-2-(2-bromomethylphenyl)-2-methoxyimino-N-methylacetamide (1.08 g; yield, 37.7%) as an oil.
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