[H-].[Na+].F[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13]1[C:17]([CH3:18])=[N:16][CH:15]=[N:14]1.[CH2:19]([OH:22])[CH:20]=[CH2:21]>CN(C=O)C>[CH2:19]([O:22][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13]1[C:17]([CH3:18])=[N:16][CH:15]=[N:14]1)[CH:20]=[CH2:21]A suspension of NaH (0.675 g, 16.88 mmol, 60% dispersion in mineral oil) in DMF (25 mL) was cooled to 0° C. A solution 1-(2-fluoro-4-nitrophenyl)-5-methyl-1H-1,2,4-triazole (2.50 g, 11.25 mmol) was added dropwise. Allyl alcohol (0.784 g, 13.5 mmol) was added via syringe over 5 min. The reaction mixture was allowed to warm up to room temperature. After 30 min, TLC showed completion of reaction. It was slowly quenched with water (10 mL), diluted with brine (100 mL), and extracted with EtOAc (3×50 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel chromatography (20-80% EtOAc/hexane, linear gradient). Pure fractions were concentrated under reduced pressure to afford 1-(2-(allyloxy)-4-nitrophenyl)-5-methyl-1H-1,2,4-triazole (1.5 g 51% yield) as a yellow-brown colored solid. LC-MS (M+H)+=261.0. 1H NMR (400 MHz, CDCl3) δ ppm 8.02-7.94 (m, 3H), 7.58 (d, 1H, J=8.4 Hz), 5.98-5.89 (m, 1H), 5.37-5.32 (m, 2 H), 4.69-4.70 (m, 2H), 2.403 (s, 3H).
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