4-Fluorophenol → Quinoxyfen

HRID 1885529Notes

Reaction equation

HRID 1885529 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-feb7b7f5ccc543dba9aba0eda0744e6d
Source dataset
uspto-grants-1992_09
Patent number
US05145843

Reaction notes

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