[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Na+].[N+]([C:14]1[CH:15]=C(S([O-])(=O)=O)C=C[CH:19]=1)([O-])=O.S(=O)(=O)(O)O>OCC(CO)O>[F:9][C:7]1[CH:6]=[C:5]2[C:3](=[C:2]([Br:1])[CH:8]=1)[N:4]=[CH:15][CH:14]=[CH:19]2To a mixture of 2-bromo-4-fluoroaniline (commercially available, 7.0 g), glycerol (7.0 g) and m-nitrobenzene sulfonic acid sodium salt (13.0 g) was added 20 ml of 70% sulfuric acid dropwise. The reaction temperature was raised to 150° C. for 4 hr. The mixture then was cooled to room temperature, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and the resulting precipitate was collected by vacuum filtration to yield 3.47 g of the title compound as a light yellow solid; MP=75-78° C.; MS (ES) m/z (relative intensity): 227 (M+H)+ (100).
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