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

HRID 1505302Notes

Reaction equation

HRID 1505302 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-b1d59979345449a0a600b4cad6d5ac13
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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