1H-1,2,4-Triazole → 1-(4-Chlorophenoxy)-3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)-2-butanone
Reaction equation
Br[CH:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6].[NH:18]1[CH:22]=[N:21][CH:20]=[N:19]1>CC(C)=O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH:2]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6])=[CH:12][CH:13]=1Participants
4
Procedure
87 g (0.27 mol) of 1-bromo-1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-butan-2-one were dissolved in 200 ml of acetone and the solution was added dropwise to a boiling solution of 46 g (0.66 mol) of 1,2,4-triazole in 200 ml of acetone. After heating the mixture under reflux for one hour, 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, the residue was crystallized with petroleum ether. 75 g (89% of theory) of 1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)-butan-2-one of melting point 60°-63° C. were obtained.
Workup
- temperatureAfter heating the mixture
- temperatureunder reflux for one hour
- customthe solvent was removed in vacuo
- washthe methylene chloride mixture was washed several times with water
- dry with materialthe organic phase was dried over sodium sulphate
- customAfter removing the solvent in vacuo
- customthe residue was crystallized with petroleum ether
Sources & evidence
- ORD record
- ord-9e43d6cc87bc4e41b4e602888c266046
- Source dataset
- uspto-grants-1983_05
- Patent number
- US04382944
Reaction notes
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