4-(Pentafluoroethyl)-2-nitrophenol → 2-Amino-4-(pentafluoroethyl)phenol

HRID 2190820Notes

Reaction equation

HRID 2190820 reaction equation
[F:1][C:2]([F:17])([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)[C:3]([F:6])([F:5])[F:4].[H][H]>[Pd].C(OCC)(=O)C>[NH2:14][C:9]1[CH:8]=[C:7]([C:2]([F:1])([F:17])[C:3]([F:4])([F:5])[F:6])[CH:12]=[CH:11][C:10]=1[OH:13]

Participants

5

Reactant 2

HCID 866510624-(Pentafluoroethyl)-2-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 866510632-Amino-4-(pentafluoroethyl)phenolYield 83.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.38 g of 4-(pentafluoroethyl)-2-nitrophenol, 15 ml of ethyl acetate and 0.15 g of 5% palladium on carbon was stirred under about one atmosphere of hydrogen at room temperature for four hours. The reaction mixture was filtered through Celite™. The filtrate was concentrated under reduced pressure. The residue was washed with hexane to give 1.02 g of 2-amino-4-(pentafluoroethyl)phenol.

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-139f96cb555649e59340aee62ace21aa
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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