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

HRID 1612968Notes

Reaction equation

HRID 1612968 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[OH:12].[H][H]>C(O)C.[Pt](=O)=O>[NH2:9][C:5]1[CH:4]=[C:3]([OH:12])[C:2]([Cl:1])=[CH:7][C:6]=1[F:8]

Participants

5

Reactant 2

HCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 1586545-Amino-2-chloro-4-fluorophenolYield 85.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-chloro-4-fluoro-5-nitrophenol (9.17 g) and platinum dioxide (500 mg) in ethanol (120 ml) was subjected to catalytic reduction with hydrogen under room temperature and atmospheric pressure until a designed amount of hydrogen was absorbed. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was extracted with ether, and the ether layer was concentrated to obtain 6.6 g of 3-amino-6-chloro-4-fluorophenol. M.P., 145°-146° C. (decomp.).

Workup

  1. customatmospheric pressure until a designed amount of hydrogen was absorbed
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. extractionThe residue was extracted with ether
  5. concentrationthe ether layer was concentrated

Sources & evidence

ORD record
ord-edadc63c175e4159a663c0fbcabe2c3e
Source dataset
uspto-grants-1993_03
Patent number
US05191105

Reaction notes

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