Styrene → trans-Stilbene

HRID 429612

Reaktionsgleichung

Reaktionsgleichung von HRID 429612
C([O-])(=O)C.[Na+].[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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:16]/[C:15]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:19]1(/[CH:18]=[CH:17]\[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:19]1([C:18]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Komponenten

9

Edukt 3

HCID 7501StyreneHCID 214133-BromoquinolineHCID 517045Sodium Acetate

Produkt 4

HCID 107401,1-DiphenylethyleneAusbeute 14,1 %HCID 214133-BromoquinolineHCID 638088trans-StilbeneAusbeute 85,1 %HCID 5356785cis-StilbeneAusbeute 0,8 %

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 (CH2CN)2PdCl2, 34.9 mg (0.09 mmol) of Ph4PCl, 496.0 mg (6.05 mmol) of anhydrous sodium acetate, 638.74 mg (3.07 mmol) of 3-bromoquinoline and 427.0 mg (4.1 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 72.5% yield of Heck products (85.1% trans-stilbene, 0.8% cis-stilbene, and 14.1% 1,1-diphenylethene) is obtained with 78.5% conversion of 3-bromoquinoline.

Quellen und Nachweise

ORD-Eintrag
ord-dd08380619e74406b89f84d676a720ba
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316675B1

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