Sodium Acetate → 3,3,3-Trifluoro-2-oxopropanal (4-chloro-2-fluoro-5-hydroxyphenylhydrazone)

HRID 1700069

Reaction equation

HRID 1700069 reaction equation
C([O-])(=O)C.[Na+].Br[CH:7](Br)[C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].Cl.[F:16][C:17]1[CH:22]=[C:21]([Cl:23])[C:20]([OH:24])=[CH:19][C:18]=1[NH:25][NH2:26]>O>[Cl:23][C:21]1[C:20]([OH:24])=[CH:19][C:18]([NH:25][N:26]=[CH:7][C:8](=[O:9])[C:10]([F:13])([F:12])[F:11])=[C:17]([F:16])[CH:22]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 5505231,1-Dibromo-3,3,3-trifluoroacetoneHCID 691421062-Fluoro-4-chloro-5-hydroxyphenylhydrazine hydrochloride

Product 1

HCID 691427153,3,3-Trifluoro-2-oxopropanal (4-chloro-2-fluoro-5-hydroxyphenylhydrazone)Yield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 49.2 g of sodium acetate and 40.5 g of 1,1-dibromo-3,3,3-trifluoroacetone were dissolved in 400 ml of water, and the solution was heated at 80° to 90° C. for 40 minutes. The solution was cooled to 0° C., to which 75 g of the crude 2-fluoro-4-chloro-5-hydroxyphenylhydrazine hydrochloride crystals obtained above was added, and the mixture was stirred at room temperature for 70 minutes. The precipitated crystals were collected by filtration and dried under reduced pressure, which afforded 35.4 g of 3,3,3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-hydroxyphenylhydrazone).

Workup

  1. temperaturethe solution was heated at 80° to 90° C. for 40 minutes
  2. customobtained
  3. additionabove was added
  4. filtrationThe precipitated crystals were collected by filtration
  5. customdried under reduced pressure, which

Sources & evidence

ORD record
ord-3b24113d82fc46688497c96b6088ac1c
Source dataset
uspto-grants-2002_02
Patent number
US06348628B1

Linked notes

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