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

HRID 5543

반응식

HRID 5543 반응식
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

참가 물질

4

반응물 2

HCID 68664,7-DichloroquinolineHCID 97324-Fluorophenol

생성물 1

HCID 1641717-Chloro-4-(4-fluorophenoxy)quinoline수율 615.9%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-02b7b388594a45e995525bf702f7126b
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245036

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