Iodine → 6-Bromo-2-chloro-3-iodoquinoline

HRID 1028932노트

반응식

HRID 1028932 반응식
[Li]CCCC.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([Cl:17])[CH:11]=[CH:10]2.[I:18]I.C1COCC1.O>C1COCC1.CCCCCC.C(OCC)C.O>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([Cl:17])[C:11]([I:18])=[CH:10]2

참가 물질

9

반응물 4

HCID 807IodineHCID 128940866-Bromo-2-chloroquinolineHCID 21881883Oxolane--water (1/1)HCID 178418339Butyllithium

생성물 1

HCID 866768376-Bromo-2-chloro-3-iodoquinoline

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

To a solution of THF (50 mL) and DIPA (1.8 mL, 12.37 mmol) at −70° C. was added n-BuLi (7.7 mL, 12.4 mmol). The mixture was allowed to stir at 0° C. for 1 h. Slow addition of 6-bromo-2-chloroquinoline (3.0 g, 12.4 mmol) in THF (50 mL) was achieved at −75° C. and the mixture was stirred at this temperature for 2 h. Iodine (3.1 g, 12.4 mmol) in 10 ml of THF was then slowly added and the reaction mixture was allowed to stir at −75° C. for 2 h before hydrolysis by THF/water (20% v/v). Water and diethyl ether were added at −10° C. and the reaction mixture was extracted with ether. The organic layer was washed with sodium thiosulfate and water, dried over MgSO4 and concentrated in vacuo to give a yellow solid which was slurried with hexane and filtered to give 6-bromo-2-chloro-3-iodoquinoline as a tan solid.

후처리

  1. customwas achieved at −75° C.
  2. stirringthe mixture was stirred at this temperature for 2 h
  3. extractionthe reaction mixture was extracted with ether
  4. washThe organic layer was washed with sodium thiosulfate and water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid which
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-70467365e91d4518bf222a527cb517e8
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735384B2

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