Iodine → 9-Iodo-10-phenylanthracene

HRID 1676415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676415
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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 149583739-Iodo-10-phenylanthraceneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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)).

Aufarbeitung

  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))

Quellen und Nachweise

ORD-Eintrag
ord-cbb472fa9b5d4eeeace4a22cc97865e5
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003977B2

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