4-Fluorophenol → Quinoxyfen

HRID 2255428Notes

Reaction equation

HRID 2255428 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:13])=[CH:9][C:10]=2[Cl:12])[N:5]=[CH:4][CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>C(OCC)(=O)C.[OH-].[Na+]>[Cl:12][C:10]1[CH:9]=[C:8]([Cl:13])[CH:7]=[C:6]2[C:11]=1[C:2]([O:21][C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=1)=[CH:3][CH:4]=[N:5]2

Participants

5

Reactant 2

HCID 97324-FluorophenolHCID 6158354,5,7-Trichloroquinoline

Product 1

HCID 3391107QuinoxyfenYield 76.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 29.11 g of 4,5,7-trichloroquinoline and 16.84 g of 4-fluorophenol was heated to 160° C. After approximately 40 minutes, the molten solution solidified. The solid was dissolved in ethyl acetate and 2N NaOH. The organic layer was washed with base to remove excess phenol, then dried. Solvent was removed by reducing pressure, and the residue was purified by recrystallizing in heptane to produce 29.49 g of the title product. M.P. 105°-106° C.

Workup

  1. washThe organic layer was washed with base
  2. customto remove excess phenol
  3. customdried
  4. customSolvent was removed
  5. customthe residue was purified
  6. customby recrystallizing in heptane

Sources & evidence

ORD record
ord-070086f1772e493ba15c826b7bd9e346
Source dataset
uspto-grants-1993_08
Patent number
US05240940

Reaction notes

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