[N:1]([CH:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[Br:16])[C:5]([F:8])([F:7])[F:6])=[N+]=[N-].C(O)=O.NN>[Ni].C(O)C>[Br:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[CH:4]([NH2:1])[C:5]([F:6])([F:7])[F:8]Add Raney Nickel (1.58 g, 26.8 mmol) to a solution of 1-(1-azido-2,2,2-trifluoro-ethyl)-2-bromo-4-fluoro-benzene (0.8 g, 2.68 mmol), formic acid (1.24 g, 26.8 mmol), and hydrazine (0.86 g, 26.8 mmol) in 10 mL of ethanol. Stir the mixture at RT for 1 h and filter off the excess Nickel. Dilute the mother liquor with water and extract with chloroform. Dry the organic layer over sodium sulfate and concentrate to give the title compound as a brown oil (0.73 g, 100%). MS (ES) m/z 272/274 [M+1]+.
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