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

HRID 1191693Notes

Reaction equation

HRID 1191693 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 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a dry flask purged with Argon was added 10% Pd/C (80 mg) followed by 3-fluoro-4-nitrophenol (1.2 g, 7.64 mmol) as a solution in ethyl acetate (40 mL). The mixture was stirred under an H2 atmosphere for 4 h. The mixture was filtered through a pad of Celite and the solvent was evaporated under reduced pressure to afford the desired product as a tan solid (940 mg, 7.39 mmol; 97% yield); 1H-NMR (DMSO-d6) 4.38 (s, 2H), 6.29-6.35 (m, 1H), 6.41 (dd, J=2.5, 12.7, 1H), 6.52-6.62 (m, 1H), 8.76 (s, 1H).

Workup

  1. customTo a dry flask purged with Argon
  2. additionwas added 10% Pd/C (80 mg)
  3. filtrationThe mixture was filtered through a pad of Celite
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-20fb08859ff34f7b85907d37994b9edb
Source dataset
uspto-grants-2014_03
Patent number
US08680124B2

Reaction notes

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