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Iodine → 9-Iodo-10-phenylanthracene

HRID 1676415
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HRID 1676415 반응식
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li]CCCC.[I:27]I.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[I:27][C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 807IodineHCID 108762Thiosulfuric acid, disodium salt, monohydrateHCID 41558369-Bromo-10-phenyl-anthraceneHCID 178418339Butyllithium

생성물 1

HCID 149583739-Iodo-10-phenylanthracene수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
2회

실험 절차

3.33 g (10 mmol) of 9-bromo-10-phenylanthracene was dissolved in 80 ml of tetrahydrofuran (abbreviation: THF), and the temperature was lowered to −78° C. 7.5 ml (12.0 mmol) of n-BuLi (1.6M) was dropped into the reaction solution by a dropping funnel, and it was stirred for 1 hour. A solution in which 5 g (20.0 mmol) of iodine was dissolved in 20 ml of THF was dropped and stirred for 2 hours at −78° C. After reaction, a sodium thiosulfate water solution was added to stop the reaction. An organic layer was washed with a sodium thiosulfate water solution and a saturated saline and dried with magnesium sulfate. After the natural filtration, the filtrate was concentrated and the obtained solid was recrystallized by ethanol. Then, 3.1 g of a light-yellow solid of 9-iodo-10-phenylanthracene, which was the intended object, was obtained with a yield of 83% (synthetic scheme of (b-5)).

후처리

  1. customwas lowered to −78° C
  2. additionwas dropped
  3. stirringstirred for 2 hours at −78° C
  4. customAfter reaction
  5. customthe reaction
  6. washAn organic layer was washed with a sodium thiosulfate water solution
  7. dry with materiala saturated saline and dried with magnesium sulfate
  8. filtrationAfter the natural filtration
  9. concentrationthe filtrate was concentrated
  10. customthe obtained solid was recrystallized by ethanol
  11. customwas obtained with a yield of 83% (synthetic scheme of (b-5))

출처 및 근거

ORD 기록
ord-cbb472fa9b5d4eeeace4a22cc97865e5
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08003977B2

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