[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].BrN1C(=O)CCC1=O.[N-:23]=[N+:24]=[N-:25].[Na+]>C(Cl)(Cl)(Cl)Cl.[Cl-].[Na+].O.N(C(C)(C)C#N)=NC(C)(C)C#N>[N:23]([CH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])=[N+:24]=[N-:25]A mixture of methyl 5-methyl-2-nitrobenzoate (5.5 g, 30 mmol), N-bromosuccinimide (NBS, 5.87 g, 33 mmol), and azobisisobutyronitrile (AlBN, 200 mg) in carbon tetrachloride (60 mL) was refluxed for 3 h. The insoluble material formed was removed by filtration and the filtrate was concentrated. The residue was dissolved in DMF (10 mL) and sodium azide (2.92 g, 45 mmol) was added. The mixture was stirred for 2 h at 50° C., poured into brine, and extracted with a 1:1 mixture of toluene and ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 4:1 hexane/ethyl acetate to give 3.97 g of the title compound (56%).
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