trans-beta-Bromostyrene → trans-Stilbene

HRID 2182833

Reaktionsgleichung

Reaktionsgleichung von HRID 2182833
[CH:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/Br)=[CH:3][CH:2]=1.[I-].[C:11]1([Zn+])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Pd].C(F)(F)(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F.C(#N)C.C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:4]1(/[CH:7]=[CH:8]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Komponenten

8

Edukt 2

HCID 5314126trans-beta-Bromostyrene2×HCID 178506617HCID 178506617, Verbindung2×

Produkt 1

HCID 638088trans-Stilbene

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23938PalladiumKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 9639PerfluorohexaneLösungsmittel

Versuchsvorschrift

In an illustrative example, a coupling reaction was conducted between (E)-2-bromostyrene (PhCH═CHBr) and phenylzinc iodide (PhZnI) promoted by a fluorous palladium catalyst. The catalyst was prepared from Pd2(dba)3 and the known fluorous phosphine (p-C6F13CH2CH2C6H4)3P. A mixture of the catalyst in FC-72 was contacted in a U-tube with a first organic phase containing (E)-2-bromostyrene in acetonitrile and a second organic phase containing phenylzinc iodide in THF. After one day at ambient temperature, each organic phase was removed and subjected to standard aqueous workup. Unreacted (E)-2-bromostyrene was recovered from the first organic phase while the coupled reaction product, (E)-stilbene (PhCH═CHPh) was isolated from the second organic phase.

Aufarbeitung

  1. customeach organic phase was removed
  2. customwas recovered from the first organic phase while the coupled reaction product

Quellen und Nachweise

ORD-Eintrag
ord-4807387aed194981af52ac32c94e23b4
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897331B2

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