Nitric Acid → 3,5-Difluoro-2-nitrophenol

HRID 889260Notes

Reaction equation

HRID 889260 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[N+:10]([O-])([OH:12])=[O:11]>ClCCl.S([O-])([O-])(=O)=O.[Ni+].[NH4+]>[F:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 759283,5-Difluorophenol

Product 1

HCID 118195353,5-Difluoro-2-nitrophenol

Reagents, catalysts & solvents 2

HCID 171000000CID 171000000CatalystHCID 6344DichloromethaneSolvent

Procedure

To a yellow solution of 3,5-difluorophenol (1.50 g, 11.5 mmol) in dichloromethane (20 mL) under a blanket of nitrogen is added ammonium nickel sulfate (4.56 g, 11.54 mmol) with vigorous stirring, followed by the addition of nitric acid (69%, 0.74 mL, 11.54 mmol). The resulting heterogeneous mixture is then stirred at ambient temperature vigorously for 30 minutes. It is filtered and dichloromethane is removed under reduced pressure. The residue is purified by column chromatography to afforded a yellow solid as the title compound.

Workup

  1. filtrationIt is filtered
  2. customdichloromethane is removed under reduced pressure
  3. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-e2823d733b634c7188c41094cebe4476
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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