3-Fluoro-4-nitrophenol → 4-Amino-3-fluorophenol

HRID 424817Notes

Reaction equation

HRID 424817 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>C(OCC)(=O)C>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([OH:11])=[CH:3][C:2]=1[F:1]

Participants

3

Reactant 1

HCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 27359194-Amino-3-fluorophenolYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-fluoro-4-nitrophenol (2.20 g, 14.0 mmol) in 25 mL ethyl acetate is evacuated under reduced pressure and filled with nitrogen three times. Palladium, 10% by weight on carbon (220 mg) is added. The mixture is evacuated under reduced pressure and filled with nitrogen three times. The mixture is evacuated under reduced pressure and filled with hydrogen. The mixture is stirred under hydrogen atmosphere (balloon) over night. The mixture is then filtered over diatomaceous earth and concentrated to provide the title compound (1.7 g, 96%) as a brown solid. 1H NMR (400 MHz, DMF-d7) δ 8.75 (s, 1H), 6.78 (m, 1H), 6.40 (m, 1H), 6.50 (m, 1H), 4.38 (s, 2H).

Workup

  1. customis evacuated under reduced pressure
  2. additionfilled with nitrogen three times
  3. additionPalladium, 10% by weight on carbon (220 mg) is added
  4. customThe mixture is evacuated under reduced pressure
  5. additionfilled with nitrogen three times
  6. customThe mixture is evacuated under reduced pressure
  7. additionfilled with hydrogen
  8. filtrationThe mixture is then filtered over diatomaceous earth
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1af83fc43bd04012902e2c06ff5820f0
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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