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

HRID 2066278Notes

Reaction equation

HRID 2066278 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), followed by stirring under a hydrogen atmosphere at room temperature for 24 hr and 20 min. The atmosphere in the reaction vessel was replaced with nitrogen to stop the reaction, and the catalyst was filtered through Celite. The filtrate was removed under reduced pressure to provide the titled compound as a brown solid (4.96 g, 99%).

Workup

  1. customthe reaction
  2. filtrationthe catalyst was filtered through Celite
  3. customThe filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-798c6ee0d4a04c2080fb0c2295d728b4
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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