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

HRID 2288650Notes

Reaction equation

HRID 2288650 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 l,l-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-a343d65606314afd920ea3b31936370f
Source dataset
uspto-grants-2000_07
Patent number
US06090753

Reaction notes

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