1,2-Difluoro-4-nitrobenzene → 1-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

HRID 1452582Notes

Reaction equation

HRID 1452582 reaction equation
[CH3:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1F.FC1C=C([N+]([O-])=O)C=CC=1N1C=C(C)N=N1>>[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1[N:4]1[CH:5]=[N:6][C:2]([CH3:1])=[N:3]1

Participants

4

Reactant 3

HCID 1230531,2-Difluoro-4-nitrobenzeneHCID 575269881-(2-Fluoro-4-nitro-phenyl)-4-methyl-[1,2,3]-triazoleHCID 178433329HCID 178433329, compound

Product 1

HCID 575269631-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazoleYield 44.7%

Procedure

3-Methyl-1,2,4-triazole (34.5 g, 0.416 mol) and 3,4-difluoronitrobenzene (46 ml, 0.416 mol) were reacted as described for Intermediate 22. Chromatography on silica gel with 5-50% ethyl acetate in hexanes and recrystallisation from ethyl acetate/hexanes gave the title compound as light yellow crystals (41.3 g), m.p. 113.8° C.-114.3° C. The other two isomers were also isolated.

Workup

  1. customChromatography on silica gel with 5-50% ethyl acetate in hexanes and recrystallisation from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fb6fdf0fba514b43af022365a87c5dc1
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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