1-Benzyloxy-2,3-difluoro-6-nitrobenzene → 4-Amino-2,3-difluorophenol

HRID 2265720Notes

Reaction equation

HRID 2265720 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[C:10]=1[F:19])C1C=CC=CC=1.C(OC1C(F)=C(F)C=CC=1[N+]([O-])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:19])[C:11]=1[F:18]

Participants

5

Reactant 2

HCID 178588811-Benzyloxy-2,3-difluoro-6-nitrobenzeneHCID 574708771-(Benzyloxy)-2,3-difluoro-4-nitrobenzene

Product 1

HCID 27787664-Amino-2,3-difluorophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of a mixture of 1-(benzyloxy)-2,3-difluoro-4-nitrobenzene and 2-(benzyloxy)-3,4-difluoro-1-nitrobenzene (6.54 g) in methanol (200 ml) was added 10% palladium on carbon (654 mg), followed by stirring under a hydrogen atmosphere at room temperature for 26 hr and 50 min. The atmosphere in the reaction vessel was replaced with nitrogen to stop the reaction, and the catalyst was filtered off through Celite. The filtrate was concentrated under reduced pressure to provide the titled compound as a black solid (3.52 g) which was a mixture of 6-amino-2,3-difluorophenol.

Workup

  1. customthe reaction
  2. filtrationthe catalyst was filtered off through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e229a6c59fc34f71a0498383adb80066
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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