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

HRID 2042035Notes

Reaction equation

HRID 2042035 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]>CCOC(C)=O.[OH-].[Pd+2].[OH-]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([F:1])=[C:3]([OH:12])[CH:4]=1

Participants

4

Reactant 1

HCID 109210242,4-Difluoro-5-nitrophenol

Product 1

HCID 27829995-Amino-2,4-difluorophenolYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2,4-difluoro-5-nitrophenol (1.01 g, 5.77 mmol) in EtOAc was added palladium hydroxide (0.08 g, 0.57 mmol) and the resulting slurry was stirred under a hydrogen atmosphere for 6 h. The mixture was filtered through a Celite® pad, washing with EtOAc (2×10 mL) and the filtrate was concentrated to afford 5-amino-2,4-difluorophenol (0.8 g, 96% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 9.28 (s, 1H), 6.91 (t, J=7.2 Hz, 1H), 6.35 (t, J=8.8 Hz, 1H), 4.84 (brs, 2H); MS (ESI) m/z: 146.0 (M+H+).

Workup

  1. filtrationThe mixture was filtered through a Celite® pad
  2. washwashing with EtOAc (2×10 mL)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cc91c06f957f4188a0cd854be3170634
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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