Реакция #5639

Уравнение реакции

4,7-dichloroquinoline

4-fluorophenol

→

product

4-(4-Fluorophenoxy)-7-chloroquinoline

Растворители

xylene

Условия реакции

Обработка

1. 1
   ДругоеTo a 50 mL flask equipped with a condenser
2. 2
   Другоеdrying tube
3. 3
   workup.ADDITIONwere added
4. 4
   ТемператураThe reaction mixure was heated
5. 5
   Температураto reflux
6. 6
   Температураmaintained at that temperature for 18 hr
7. 7
   ФильтрацияThe reaction mixture was filtered hot
8. 8
   Другоеto remove the polymer
9. 9
   ТемператураAfter cooling
10. 10
    Промывкаthe filtrate was washed with 50 mL of 5N NaOH
11. 11
    ЭкстракцияThe caustic layer was extracted with 2×25 mL of diethyl ether
12. 12
    Сушкаdried over Na2SO4
13. 13
    ДругоеRemoval of the solvent

Методика

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.

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