[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].[Cl-].[Cl-].[Cl-].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:10])[NH:13][N:12]=[N:11]2)=[CH:4][CH:3]=1To a solution of 1-bromo-4-isocyanatobenzene (5.00 g, 25.4 mmol) in THF (30 mL) was added sodium azide (5.00 g, 76.9 mmol) followed by the addition of a solution of aluminum trichloride (4.00 g, 30.3 mmol) in THF (18 mL) slowly. The reaction mixture was heated to reflux overnight. After cooling to rt, the reaction was quenched with H2O (50 mL). The organic solvent was removed under reduced pressure. The solids were collected by filtration to obtain compound 14a as a white solid (4.50 g, 71% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C2H5BrN4O: 241.0 (M+H). Found 241.1.
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