Dibenzothiophene → 2-Bromodibenzothiophene

HRID 241492

Reaktionsgleichung

Reaktionsgleichung von HRID 241492
C1C2C3C=CC=CC=3SC=2C=CC=1.BrBr.O.S([O-])([O-])=O.[Na+].[Na+].Br[C:24]1[CH:37]=[CH:36][C:27]2[S:28][C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=3[C:26]=2[CH:25]=1>C(Cl)(Cl)Cl>[Br:35][C:32]1[CH:33]=[CH:34][C:29]2[S:28][C:27]3[CH:36]=[CH:37][CH:24]=[CH:25][C:26]=3[C:30]=2[CH:31]=1

Komponenten

6

Edukt 4

HCID 3023Dibenzothiophene2×HCID 24408BromineHCID 6311202,8-DibromodibenzothiopheneHCID 86645562Sodium sulphite monohydrate

Produkt 1

HCID 2995082-Bromodibenzothiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Dibenzothiophene (15 g, 79.9 mmol) was dissolved in 1.5 L chloroform. To the solution, bromine (12.76 g, 79.9 mmol) was added dropwise. The reaction mixture was vigorously stirring for 2 days at room temperature and then treated with sodium sulfite water solution. The organic phase was evaporated to give a white solid which has 48% unreacted dibenzothiophene, 50% 2-bromodibenbzothiophene and less 2% 2,8-dibromodibenzothiophene based on GC-MS and HPLC results. The mixture was repeatedly recrystallized with ethyl acetate to get pure 2-bromodibenzothiophene.

Aufarbeitung

  1. customThe organic phase was evaporated
  2. customto give a white solid which
  3. customresults
  4. customThe mixture was repeatedly recrystallized with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c8a2086a4f7c400aa766e068b132d21f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08652653B2

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