[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:8]([CH2:25][CH2:26][CH2:27][CH3:28])=[N:9][N:10]([C:15]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=3[Cl:24])[C:11]=2[C:12](O)=[O:13])=[C:4]([F:31])[CH:3]=1.S(Cl)([Cl:34])=O.Cl>C1CCCCC1>[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:8]([CH2:25][CH2:26][CH2:27][CH3:28])=[N:9][N:10]([C:15]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=3[Cl:24])[C:11]=2[C:12]([Cl:34])=[O:13])=[C:4]([F:31])[CH:3]=1A mixture of 672 mg (1.32 mmol) of 4-(4-bromo-2-fluorobenzyl)-3-n-butyl-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carboxylic acid (from Step C), 2.3 mL of thionyl chloride, and 6 mL of cyclohexane was stirred at reflux under N2 for 4 hours, during which time HCl gas was evolved. The cooled solution was concentrated in vacuo to yield an orange oil, which was used directly in the next step.
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