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

HRID 1636681Notes

Reaction equation

HRID 1636681 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-805aa0a200f940a584a03de107af81d5
Source dataset
uspto-grants-2000_03
Patent number
US06034248

Reaction notes

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