[N:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])=[N+:2]=[N-:3].[CH3:14][CH:15]([CH3:20])[C:16]#[C:17][Mg]Cl.CC(C)C#C.C([Mg]Cl)(C)C>C1COCC1>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[C:4]([N:1]2[C:16]([CH:15]([CH3:20])[CH3:14])=[CH:17][N:3]=[N:2]2)[CH:9]=1A 30 mL scintillation vial was charged with 2-azido-4-chloro-1-nitrobenzene (200 mg, 1.0 mmol) and 0.75 M 3-methyl-1-butynylmagnesium chloride in THF (1.6 mL, 1.2 mmol; prepared by mixing 3-methyl-1-butyne (120 μL, 1.2 mmol) and iPrMgCl (1.5 mL, 1.0 M in THF) at room temperature, heating to 40° C. for 30 minutes then cooling to room temperature). The reaction was allowed to stir at room temperature for 1 hour after which the reaction was quenched with SiO2 and the solvent removed. The product (adsorbed to SiO2) was then loaded on a SiO2 column and purified to give 1-(5-chloro-2-nitro-phenyl)-5-isopropyl-1H-[1,2,3]triazole.
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