[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[N+]([O-])=O)=[CH:8][CH:7]=1>CS(C)=O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:1]=[N:2][NH:3][CH:13]=2)=[CH:8][CH:7]=1Sodium azide (4.28 g, 65.8 mmol) was added to a solution (E)-1-fluoro-4-(2-nitro-vinyl)-benzene (1.00 g, 5.98 mmol) in DMSO (50 mL), the solution was stirred at room temperature for 14 hours and the reaction mixture was poured onto water. The aqueous phase was extracted with AcOEt. The organic phase was washed with saturated solution of NaHCO3, brine, dried over MgSO4, filtered and evaporated to yield 300 mg (1.84 mmol, 31%) of 4-(4-fluoro-phenyl)-1H-[1,2,3]triazole.
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