1H-1,2,4-Triazole → 1-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)-2-butanone

HRID 2198773Notes

Reaction equation

HRID 2198773 reaction equation
Br[CH:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6].[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1>C(#N)C>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[O:10][CH:2]([N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6]

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 130194441-Bromo-1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone

Product 1

HCID 128998841-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)-2-butanoneYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

96.3 g (0.27 mol) of 1-bromo-1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone were dissolved in 200 ml of acetonitrile and the solution was added dropwise to a boiling solution of 46 g (0.56 mol) of 1,2,4-triazole in 200 ml of acetonitrile. After heating the mixture under reflux for 20 hours, the solvent was removed in vacuo, the residue was taken up in methylene chloride, the methylene chloride mixture was washed several times with water and the organic phase was dried over sodium sulphate. After removing the solvent in vacuo, 83 g (89% of theory) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)-2-butanone were obtained as an oil, which was further reacted directly. ##STR84##

Workup

  1. temperatureAfter heating the mixture
  2. temperatureunder reflux for 20 hours
  3. customthe solvent was removed in vacuo
  4. washthe methylene chloride mixture was washed several times with water
  5. dry with materialthe organic phase was dried over sodium sulphate
  6. customAfter removing the solvent in vacuo

Sources & evidence

ORD record
ord-59c9c46fa7724b25be32a56efa0b2e6b
Source dataset
uspto-grants-1982_11
Patent number
US04359470

Reaction notes

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