2-Fluoro-4-nitrophenol → Phenol, 4-amino-2-fluoro-

HRID 520711Notes

Reaction equation

HRID 520711 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11]>CO.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([OH:11])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 98252-Fluoro-4-nitrophenol

Product 1

HCID 2735918Phenol, 4-amino-2-fluoro-Yield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-4-nitrophenol (5.0 g, 31.8 mmol) in methanol (200 mL) was added Pd/C (1.0 g, 10%). The reaction was stirred at rt overnight in a H2 atmosphere. The mixture was filtered through a pad of CELITE®, then washed with MeOH (5 mL). The filtrate was concentrated in vacuo to give the title compound as a brown solid (4.02 g, >99%).

Workup

  1. filtrationThe mixture was filtered through a pad of CELITE®
  2. washwashed with MeOH (5 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-40331ac9960846ddacc54133c4ec0b79
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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