4,7-Dichloroquinoline → 7-Chloro-4-(4-fluorophenoxy)quinoline

HRID 5543

Reaktionsgleichung

Reaktionsgleichung von HRID 5543
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1>C1(C)C(C)=CC=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[C:11]3[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 68664,7-DichloroquinolineHCID 97324-Fluorophenol

Produkt 1

HCID 1641717-Chloro-4-(4-fluorophenoxy)quinolineAusbeute 615,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

To a 50 mL flask equipped with a condenser, drying tube and thermometer, was added 1.98 g (0.01 moles) of 4,7-dichloroquinoline, 1.07 g (0.0015 moles) of polyDMAP™and 20 mL of xylene. The mixture was stirred to reswell the polymer and 1.57 g (0.0014 moles) of 4-fluorophenol were added. The reaction mixure was heated to reflux and maintained at that temperature for 18 hr. The reaction mixture was filtered hot to remove the polymer. After cooling, the filtrate was washed with 50 mL of 5N NaOH. The caustic layer was extracted with 2×25 mL of diethyl ether. The xylene and the ether layers were combined and dried over Na2SO4. Removal of the solvent provided 2.36 g (86 percent yield) of product, mp=89°-91° C.

Aufarbeitung

  1. customTo a 50 mL flask equipped with a condenser
  2. customdrying tube
  3. additionwere added
  4. temperatureThe reaction mixure was heated
  5. temperatureto reflux
  6. temperaturemaintained at that temperature for 18 hr
  7. filtrationThe reaction mixture was filtered hot
  8. customto remove the polymer
  9. temperatureAfter cooling
  10. washthe filtrate was washed with 50 mL of 5N NaOH
  11. extractionThe caustic layer was extracted with 2×25 mL of diethyl ether
  12. dry with materialdried over Na2SO4
  13. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-02b7b388594a45e995525bf702f7126b
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245036

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