4-Bromoanisole → 1-(4-methoxyphenyl)-1H-1,2,4-triazole

HRID 903991Notes

Reaction equation

HRID 903991 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]Cl.CN(C)C=O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 77304-BromoanisoleHCID 92571H-1,2,4-TriazoleHCID 11430Potassium Carbonate

Product 1

HCID 110843901-(4-methoxyphenyl)-1H-1,2,4-triazoleYield 44.5%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 13.8 parts of 1H-1,2,4-triazole, 18.7 parts of 1-bromo-4-methoxybenzene, 5 parts of potassium carbonate, 0.5 parts of copper (I)chloride and 90 parts of N,N-dimethylformamide is stirred and refluxed for 2 days. The reaction mixture is cooled and poured onto water. The product is extracted twice with benzene. The combined extracts are washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated. The residue is triturated in 2,2'-oxybispropane. The product is filtered off and dried, yielding 7.8 parts (44.5%) of 1-(4-methoxyphenyl)-1H-1,2,4-triazole; mp. 99.4° C.

Workup

  1. temperaturerefluxed for 2 days
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted twice with benzene
  5. washThe combined extracts are washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe residue is triturated in 2,2'-oxybispropane
  13. filtrationThe product is filtered off
  14. customdried

Sources & evidence

ORD record
ord-32c7e2ee56894d7db1d40600975bcc04
Source dataset
uspto-grants-1980_10
Patent number
US04229581

Reaction notes

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