p-Fluoronitrobenzene → 3-Chloro-5-fluorophenyl 4-nitrophenyl ether

HRID 1023506Notes

Reaction equation

HRID 1023506 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.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]=[C:6]([F:8])[CH:7]=[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 27737133-Chloro-5-fluorophenol

Product 1

HCID 672358223-Chloro-5-fluorophenyl 4-nitrophenyl etherYield 88.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-5-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) and the reaction mixture was heated to reflux for 4 hours. After filtration, the solvent was removed. The residue obtained was washed with n-hexane (2 times 15 mL) and dried to afford the title compound (2.38 g) which was directly used in the next step.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationAfter filtration
  4. customthe solvent was removed
  5. customThe residue obtained
  6. washwas washed with n-hexane (2 times 15 mL)
  7. customdried

Sources & evidence

ORD record
ord-dd2b611e9da64415b595deecef9380eb
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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