Styrene → trans-Stilbene

HRID 429611

Reaktionsgleichung

Reaktionsgleichung von HRID 429611
[C:1]([O-])(=O)[CH3:2].[Na+].[CH2:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].CN(C=O)C>[C:8]1(/[CH:7]=[CH:6]/[C:1]2[CH:2]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:8]1(/[CH:7]=[CH:6]\[C:1]2[CH:2]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:8]1([C:7]([C:1]2[CH:2]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH2:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

7

Edukt 2

HCID 7501StyreneHCID 517045Sodium Acetate

Produkt 3

HCID 107401,1-DiphenylethyleneAusbeute 14,5 %HCID 638088trans-StilbeneAusbeute 85 %HCID 5356785cis-StilbeneAusbeute 0,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 164911Tetraphenylphosphonium ChlorideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A reaction is performed as described in Example 1, except that 3.9 mg (0.015 mmol) of (CH3CN)2PdCl2, 34.9 mg (0.09 mmol) of Ph4PCl, 520.9 mg (6.35 mmol) of anhydrous sodium acetate, 499.6 mg (3.118 mmol) of Br-benzene and 489.3 mg (4.7 mmol) of styrene are reacted in 1.5 ml of DMF. Stirring is performed at 130° C. for 5 hours. According to the processing described in Example 1, a 74.8% yield of Heck products (85.0% trans-stilbene, 0.5% cis-stilbene, and 14.5% 1,1-diphenylethene) is obtained with 74.6% conversion of Br-benzene.

Quellen und Nachweise

ORD-Eintrag
ord-1d4146d68dbd45f885d469d03ee4ecc5
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316675B1

Verknüpfte Notizen

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