p-Fluoronitrobenzene → HCID 21528662, compound

HRID 1505304Notes

Reaction equation

HRID 1505304 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([O:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 757903-Chloro-4-fluorophenol

Product 1

HCID 21528662HCID 21528662, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-4-fluorophenol (1.46 g, 10 mmol) and 1-fluoro-4-nitrobenzene (1.41 g, 10 mmol) in acetonitrile (40 mL) was added potassium carbonate (2.76 g, 20 mmol). The reaction mixture was heated at reflux for 4 hours. After filtration, the solvent was removed to give a residue. The residue was washed with n-hexane (2 times 15 mL) and dried to afford the title compound (2.48 g) which was directly used in the next step.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. filtrationAfter filtration
  4. customthe solvent was removed
  5. customto give a residue
  6. washThe residue was washed with n-hexane (2 times 15 mL)
  7. customdried

Sources & evidence

ORD record
ord-24093ead7b0b464d9ae569154fc6fb01
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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