9-Phenylanthracene → 9-Bromo-10-phenyl-anthracene

HRID 1676414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676414
[C:1]1([C:7]2[C:8]3[C:13]([CH:14]=[C:15]4[C:20]=2[CH:19]=[CH:18][CH:17]=[CH:16]4)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21]Br.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:21][C:14]1[C:15]2[C:20]([C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]3[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]3)=[CH:19][CH:18]=[CH:17][CH:16]=2

Komponenten

5

Edukt 3

HCID 117669-PhenylanthraceneHCID 24408BromineHCID 108762Thiosulfuric acid, disodium salt, monohydrate

Produkt 1

HCID 41558369-Bromo-10-phenyl-anthraceneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 ml of carbon tetrachloride, and a solution in which 3.80 g (21.1 mmol) of bromine was dissolved in 10 ml of carbon tetrachloride was dropped into the reaction solution by a dropping funnel. After the dropping, stirring was conducted for 1 hour at room temperature. After reaction, a sodium thiosulfate water solution was added and the reaction was stopped. An organic layer was washed with an NaOH water solution and a saturated saline and dried with magnesium sulfate. After the natural filtration, it was concentrated, dissolved in toluene, and filtered through florisil, Celite (registered trademark), and alumina. The filtrate was concentrated and recrystallized by dichloromethane and hexane. Then, 7.0 g of a light-yellow solid of 9-bromo-10-phenylanthracene, which was the intended object, was obtained with a yield of 89% (synthetic scheme of (b-4)).

Aufarbeitung

  1. additionwas dropped into the reaction solution by a dropping funnel
  2. customAfter reaction
  3. washAn organic layer was washed with an NaOH water solution
  4. dry with materiala saturated saline and dried with magnesium sulfate
  5. filtrationAfter the natural filtration, it
  6. concentrationwas concentrated
  7. dissolutiondissolved in toluene
  8. filtrationfiltered through florisil, Celite (registered trademark), and alumina
  9. concentrationThe filtrate was concentrated
  10. customrecrystallized by dichloromethane and hexane
  11. customwas obtained with a yield of 89% (synthetic scheme of (b-4))

Quellen und Nachweise

ORD-Eintrag
ord-e7014530fe044d5db11395c7f2d02115
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003977B2

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