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

HRID 658448Notes

Reaction equation

HRID 658448 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>CCOC(C)=O>[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 a solution of 3-fluoro-4-nitrophenol (1.2 g, 7.64 mmol) in EtOAc (40 mL). The mixture was stirred under an H2 atmosphere for 4 h and filtered through a pad of Celite®. The filtrate 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) δ 8.76 (s, 1H), 6.62 to 6.52 (m, 1H), 6.41 (dd, J=2.5, 12.7 Hz, 1H), 6.35 to 6.29 (m, 1H), 4.38 (s, 2H).

Workup

  1. customTo a dry flask purged with argon
  2. additionwas added 10% Pd/C (80 mg)
  3. filtrationfiltered through a pad of Celite®
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-35ca654471564b8fb4c7973f796bc9e3
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

Loading…