2,6-Difluoro-4-nitrophenol → 4-Amino-2,6-difluorophenol

HRID 1885181Notes

Reaction equation

HRID 1885181 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[OH:12].[H][H]>[Pd].C(O)C>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([F:11])[C:3]=1[OH:12]

Participants

5

Reactant 2

HCID 6002102,6-Difluoro-4-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 27787644-Amino-2,6-difluorophenolYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,6-Difluoro-4-nitrophenol (1.75 g, 10 mmol) and 10% palladium on carbon catalyst (0.3 g) in ethanol (100 ml) were shaken in a closed vessel under an initial hydrogen pressure of 3.5 bar. When hydrogen uptake was complete, the catalyst was filtered off, and the filtrate evaporated to a solid, triturated with petroleum ether, filtered, washed and dried to give the title compound (1.31 g), m.p. indeterminate.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate evaporated to a solid
  3. customtriturated with petroleum ether
  4. filtrationfiltered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-2004720427a641f4b62a6a145eb2c2fe
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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