[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Br:11])[C:3]=1[CH:4]=O.Cl.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][NH2:21].C([O-])(=O)C.[Na+]>CO>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][N:21]=[CH:4][C:3]1[C:2]([Br:1])=[CH:9][C:8]([CH3:10])=[CH:7][C:6]=1[Br:11]2,6-Dibromo-4-methylbenzaldehyde (600 g, 2.16 mmol), (2-fluorophenyl)hydrazine hydrochloride (351 mg, 2.16 mmol) and sodium acetate (180 mg, 2.19 mmol) were heated in methanol (15 mL) under reflux for 2 hours. The methanol was evaporated and the residue partitioned between dichloromethane (30 mL) and aqueous brine (30 mL). The organic phase was separated, combined with additional dichloromethane extracts (2×15 mL), washed with aqueous sodium bicarbonate (2×15 mL), passed through a hydrophobic frit and evaporated to the title compound (767 mg).
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