Water → 3,3,3-Trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone)
Reaction equation
C([O-])(=O)C.[Na+].O.Br[CH:8](Br)[C:9]([C:11]([F:14])([F:13])[F:12])=[O:10].[F:16][C:17]1[CH:22]=[C:21]([Cl:23])[C:20]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:19][C:18]=1[NH:28][NH2:29]>C(OCC)C>[Cl:23][C:21]1[C:20]([O:24][CH:25]([CH3:26])[CH3:27])=[CH:19][C:18]([NH:28][N:29]=[CH:8][C:9](=[O:10])[C:11]([F:14])([F:13])[F:12])=[C:17]([F:16])[CH:22]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 70° C. for 20 minutes. Then, the reaction mixture was cooled to room temperature, to which a solution of 5.8 g (21.5 mmol) of 2-fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 ml of diethyl ether was added, and the reaction mixture was stirred at room temperature for 1 hour. The ether layer was separated, washed once with 10 ml of saturated sodium chloride solution, and dried with magnesium sulfate. The diethyl ether was distilled out, which afforded 6.5 g (20.0 mmol) of 3,3,3-trifluoro-2-oxo-propanal 1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone).
Workup
- additionwas added
- customThe ether layer was separated
- washwashed once with 10 ml of saturated sodium chloride solution
- dry with materialdried with magnesium sulfate
- distillationThe diethyl ether was distilled out
Sources & evidence
- ORD record
- ord-4927f50e869d4273918b4e947c4a7a61
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090753
Reaction notes
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