[N+:1]([C:4]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=1N)([O-:3])=[O:2].N([O-])=O.[Na+].[BrH:18]>C(O)(=O)C.S(=O)(=O)(O)O.O.[Cu](Br)Br>[Br:18][C:5]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=1[N+:1]([O-:3])=[O:2]
A solution of 2,3-dinitroaniline (2.27 g, 12.4 mmol) in 35 mL of glacial acetic acid was added dropwise to a stirred and cooled solution of sodium nitrite (0.95 g, 13.8 mmol) in concentrated sulfuric acid (7 mL) while the temperature of the reaction was held at 15-20° C. The resulting diazonium solution was then added over a five minute period to a stirred solution of copper bromide (1.85 g, 12.9 mmol) in a mixture of HBr (48%) (10 mL) and water (10 mL) heated at 75° C.-80° C. After the addition, the mixture was cooled to room temperature and added to water (500 mL). The light-green powder was filtered from the solution and dried in vacuum at room temperature to give the desired product 1-bromo-2,3-dinitrobenzene (3.0 g, 99%). This product was used in subsequent reaction without further purification. See, Donald L. Vivian J. Org. Chem. 1956, 21, 1188.
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