Tetrahydrofuran → 4-Amino-3-fluorophenol

HRID 492733Notes

Reaction equation

HRID 492733 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.O1CCCC1>C(O)C.[C].[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([OH:11])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 27359194-Amino-3-fluorophenolYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-fluoro-4-nitrophenol (20 g) in ethanol (200 ml)-tetrahydrofuran (125 ml) was added 10% palladium carbon (6.0 g), followed by stirring under a hydrogen atmosphere at room temperature for 4.5 hrs. The mixture was filtered to remove the catalyst, which was washed with ethanol. The filtrate was concentrated under a reduced pressure to provide the titled compound (16.1 g, 100%) as a pale yellow solid.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst, which
  3. washwas washed with ethanol
  4. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-6197ff38b3c9499a9fcc3286661ff60d
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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