p-Fluoronitrobenzene → 2-(4-nitrophenyl)-2h-1,2,3-triazole

HRID 279163Notes

Reaction equation

HRID 279163 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[N:12]1>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:12]2[N:13]=[CH:14][CH:15]=[N:11]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 178418936HCID 178418936, compound

Product 1

HCID 2781582-(4-nitrophenyl)-2h-1,2,3-triazoleYield 66.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Fluoronitrobenzene (21 g) was reacted with 1H-1,2,3-triazole (12.4 g) in the same manner as in Reference Example 9. The resultant was cooled and poured into water. The precipitated crystals were collected by filtration and purified by silica gel chromatography (eluent: dichloromethane to dichloromethane/acetone=8/1). The first eluted fraction was recrystallized from dichloromethane-diisopropyl ether to give 2-(4-nitrophenyl)-2H-1,2,3-triazole (18.8 g) as pale yellow prisms.

Workup

  1. temperatureThe resultant was cooled
  2. filtrationThe precipitated crystals were collected by filtration
  3. custompurified by silica gel chromatography (eluent: dichloromethane to dichloromethane/acetone=8/1)
  4. customThe first eluted fraction was recrystallized from dichloromethane-diisopropyl ether

Sources & evidence

ORD record
ord-fbd7cc109d7e47a9a9616d1326ba7ffc
Source dataset
uspto-grants-2002_03
Patent number
US06362206B1

Reaction notes

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