Reaktion #5639

Reaktionsgleichung

4,7-dichloroquinoline

4-fluorophenol

→

product

4-(4-Fluorophenoxy)-7-chloroquinoline

Lösungsmittel

xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 50 mL flask equipped with a condenser
2. 2
   Sonstigedrying tube
3. 3
   workup.ADDITIONwere added
4. 4
   TemperaturThe reaction mixure was heated
5. 5
   Temperaturto reflux
6. 6
   Temperaturmaintained at that temperature for 18 hr
7. 7
   FiltrationThe reaction mixture was filtered hot
8. 8
   Sonstigeto remove the polymer
9. 9
   TemperaturAfter cooling
10. 10
    Waschenthe filtrate was washed with 50 mL of 5N NaOH
11. 11
    ExtraktionThe caustic layer was extracted with 2×25 mL of diethyl ether
12. 12
    Trocknendried over Na2SO4
13. 13
    SonstigeRemoval of the solvent

Vorschrift

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.

Quelle