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

HRID 870425Notes

Reaction equation

HRID 870425 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.C1COCC1.[Pd]>[NH2:16][C:12]1[C:13]([F:15])=[CH:14][C:9]([OH:8])=[C:10]([F:19])[CH:11]=1

Participants

5

Reactant 1

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

Product 1

HCID 27787624-Amino-2,5-difluorophenolYield 86.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
32 °C

Procedure

To a suspension of 1-(benzyloxy)-2,5-difluoro-4-nitrobenzene (1.06 g, 4 mmol) in CH3OH (25 mL) and THF (5 mL) was added Pd/C (50% Pd content, 185 mg). The reaction was stirred at 32° C. under H2 atmosphere for 10 hours. The mixture was filtered through a CELITE® pad and the filtrate was concentrated in vacuo. The residue was washed with DCM (15 mL) to give the title compound as a dark brown solid (500 mg, 86%).

Workup

  1. filtrationThe mixture was filtered through a CELITE® pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThe residue was washed with DCM (15 mL)

Sources & evidence

ORD record
ord-6b82b07902af4e8daeabe21b00a994ab
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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