2,4-Difluoro-5-nitrophenol → 5-Amino-2,4-difluorophenol

HRID 1736238Notes

Reaction equation

HRID 1736238 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[OH:12].[H][H]>C(OCC)(=O)C.[C].[Pd]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([F:1])=[C:3]([OH:12])[CH:4]=1

Participants

5

Reactant 2

HCID 109210242,4-Difluoro-5-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 27829995-Amino-2,4-difluorophenolYield 96.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

24.9 g (142 mmol) of the resulting 2,4-difluoro-5-nitrophenol was dissolved in 150 ml of ethyl acetate, 5.0 g of 10% palladium-carbon was added and the mixture was stirred at 50° to 60° C. for 27 hours under a stream of hydrogen. The reaction vessel was filled with nitrogen, the reaction solution was filtered by means of suction, the solvent was distilled off under reduced pressure, and the residue was triturated with n-hexane to give 19.8 g (96%) of 5-amino-2,4-difluorophenol.

Workup

  1. additionThe reaction vessel was filled with nitrogen
  2. filtrationthe reaction solution was filtered by means of suction
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-b0e37f83e06e425c9dfef68edad20d34
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

Loading…