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

HRID 2265708Notes

Reaction equation

HRID 2265708 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-b60ef39cb1e842b4af7e9c8a8f7e7ba9
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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