Phenol, 2-chloro-4-fluoro-5-nitro- → 3-Amino-4-fluorophenol

HRID 2060703Notes

Reaction equation

HRID 2060703 reaction equation
Cl[C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[OH:12]>CCO.[Pd]>[NH2:9][C:5]1[CH:4]=[C:3]([OH:12])[CH:2]=[CH:7][C:6]=1[F:8]

Participants

4

Reactant 1

HCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

Product 1

HCID 135191803-Amino-4-fluorophenolYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Chloro-4-fluoro-5-nitrophenol (85 g, 0.45 mol) and 10% Pd/C (25 g, 0.023 mol) were combined in EtOH and hydrogenated (50 psi) for 12 h. The reaction mixture was filtered. The filtrate was concentrated in vacuo and purified by silica gel chromatography to provide 3-amino-4-fluorophenol (40 g 70% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.87 (s, 1H), 6.70 (dd, J=11.2, 8.8 Hz, 1H), 6.14 (dd, J=7.8, 2.4 Hz, 1H), 5.84 (m, 1H), 4.92 (s, 2H); MS (ESI) m/z: 128.2 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c84fee0bd7f340acbda3dc7eca50a923
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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