3,5-Dibromostyrene → 3,5-Dibromoethylbenzene

HRID 1822316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1822316
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH2:9])[CH:5]=[C:4]([Br:10])[CH:3]=1>C1COCC1.[OH-].[OH-].[Pd+2]>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1

Komponenten

4

Edukt 1

HCID 186903433,5-Dibromostyrene

Produkt 1

HCID 187118073,5-DibromoethylbenzeneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1,3-dibromo-5-vinyl-benzene (4.55 g, 17.4 mmol) and 20% Pd(OH)2/C (2.0 g) in THF (60 mL) is purged with N2 and then H2, and the mixture is stirred under a H2 balloon at rt for 5 hours. The mixture is filtered through hyflo, and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 15/1 hexanes/ethyl acetate to afford 3.38 g (74%) of the title compound. Rf=0.63 (9/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3).

Aufarbeitung

  1. customis purged with N2
  2. filtrationThe mixture is filtered through hyflo
  3. customthe solvent is removed in vacuo
  4. customto afford crude product that
  5. customis absorbed on silica gel
  6. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f6d75667a6c5418683af7cfd0c660276
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608639B2

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