Trifluoroacetic acid → 2-[2-chloro-4-fluoro-5-(3-difluoromethyl-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionic acid
Reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:23](=[O:24])[N:22]([CH3:25])[C:21]([CH:26]([F:28])[F:27])=[N:20]2)=[CH:14][C:3]=1[O:4][CH:5]([CH3:13])[C:6]([O:8]C(C)(C)C)=[O:7].FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:23](=[O:24])[N:22]([CH3:25])[C:21]([CH:26]([F:28])[F:27])=[N:20]2)=[CH:14][C:3]=1[O:4][CH:5]([CH3:13])[C:6]([OH:8])=[O:7]Participants
3
Procedure
A mixture of 0.8 g (0.002 mole) of tert-butyl 2-[2-chloro-4-fluoro-5-(3-difluoromethyl-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate and 59.2 g (0.52 mole) of trifluoroacetic acid was stirred at room temperature for two hours. Most of the trifluoroacetic acid was removed from the mixture by distillation under reduced pressure leaving a residue. This residue was partitioned between methylene chloride and water. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 0.5 g of 2-[2-chloro-4-fluoro-5-(3-difluoromethyl-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionic acid as an oil.
Workup
- customMost of the trifluoroacetic acid was removed from the mixture by distillation under reduced pressure
- customleaving a residue
- customThis residue was partitioned between methylene chloride and water
- dry with materialThe organic phase was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe filtrate was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-0742690714c54223905aac77635dcb89
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04919708
Reaction notes
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