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

HRID 2042055Notes

Reaction equation

HRID 2042055 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, 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. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f5ea4215e2e74e63a9ec0e2bf4302b7a
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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