1-(Benzyloxy)-2,5-difluoro-4-nitrobenzene → 4-Amino-2,5-difluorophenol

HRID 388514Notes

Reaction equation

HRID 388514 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=1[F:19])C1C=CC=CC=1>CO.[Pd]>[NH2:16][C:12]1[C:13]([F:15])=[CH:14][C:9]([OH:8])=[C:10]([F:19])[CH:11]=1

Participants

4

Reactant 1

HCID 574708681-(Benzyloxy)-2,5-difluoro-4-nitrobenzene

Product 1

HCID 27787624-Amino-2,5-difluorophenolYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(benzyloxy)-2,5-difluoro-4-nitrobenzene (9.21 g) in methanol (300 ml) was added 10% palladium on carbon (921 mg), and the mixture was stirred at room temperature for 24 hours and 20 minutes under a hydrogen atmosphere. After terminating the reaction by substituting the atmosphere in the flask with nitrogen, the catalyst was filtered using Celite. The filtrate was distilled off under reduced pressure to give the title compound (4.96 g, 99%) as a brown solid.

Workup

  1. customAfter terminating
  2. customthe reaction
  3. filtrationthe catalyst was filtered
  4. distillationThe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9becd02f3430401c961afb6112be4201
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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