p-Fluoronitrobenzene → 1-[4-(4-Nitrophenoxy)phenyl]-1H-[1,2,4]triazole

HRID 896479Notes

Reaction equation

HRID 896479 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[N:11]1([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:22][C:19]2[CH:18]=[CH:17][C:16]([N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)=[CH:21][CH:20]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1100644-(1,2,4-Triazol-1-yl)phenol

Product 1

HCID 220253681-[4-(4-Nitrophenoxy)phenyl]-1H-[1,2,4]triazoleYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-fluoro-4-nitrobenzene (0.17 mL, 1.6 mmol), 4-{[1,2,4]triazol-1-yl}phenol (0.26 g, 1.58 mmol), and potassium carbonate (1.69 g, 12.2 mmol) in DMF was refluxed overnight. The reaction was cooled to room temperature, then partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with an aqueous sodium hydroxide solution (2N), water (2 times), dried over sodium sulfate, filtered, and evaporated under reduced pressure to give a yellow solid. Purification by column chromatography (silica gel; 1:1 hexane/ethyl acetate) and recrystallization from chloroform/hexane afforded 165 mg (37%) of the title compound as a yellow solid, mp 131-132° C. 1H-NMR (CDCl3): δ 8.55 (s, 1H), 8.25 (d, J=9 Hz, 2H), 8.12 (s, 1H), 7.75 (d, J=9 Hz, 2H), 7.24 (d, J=9 Hz, 2H), 7.08 (d, J=9 Hz, 2H).

Workup

  1. temperaturewas refluxed overnight
  2. custompartitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with an aqueous sodium hydroxide solution (2N), water (2 times)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give a yellow solid
  9. customPurification
  10. customby column chromatography (silica gel; 1:1 hexane/ethyl acetate) and recrystallization from chloroform/hexane

Sources & evidence

ORD record
ord-944af804067b443ab466a4977f2bba6b
Source dataset
uspto-grants-2005_07
Patent number
US06919363B2

Reaction notes

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