C(N(CC)CC)C.[Br:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:10]=1[C:11]([NH2:13])=O.O>O=P(Cl)(Cl)Cl>[Br:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[C:10]=1[C:11]#[N:13]Triethylamine (2.53 mL, 18.2 mmol) was added to a suspension of 2-bromo-3-fluoro-6-nitrobenzamide (Example 6e) (1.60 g, 6.08 mmol) in POCl3 (32 mL), and the mixture was heated at 75° C. for 1.5 h. The mixture was carefully poured into a mixture of ice and water (400 mL) and extracted twice with CH2Cl2. The combined extract was dried MgSO4, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel eluting with solvent gradient 0% to 100% EtOAc in hexanes, to give 2-bromo-3-fluoro-6-nitrobenzonitrile 0.95 g, (64%) as a yellow solid.
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