tert-Butylphosphine → 2-(4'-Vinyl-biphenyl-2-yl)pyridine

HRID 1639947

Reaktionsgleichung

Reaktionsgleichung von HRID 1639947
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[CH2:2].Cl[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.F[K].C(P)(C)(C)C>C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd].O1CCOCC1>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:5][CH:4]=1)=[CH2:2]

Komponenten

7

Edukt 4

HCID 123165tert-ButylphosphineHCID 27343934-Vinylphenylboronic acidHCID 111481852-(2-Chloro-phenyl)pyridineHCID 178506427HCID 178506427, Verbindung

Produkt 1

HCID 667224412-(4'-Vinyl-biphenyl-2-yl)pyridineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44556509Tris(dibenzylideneacetone) palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

This Example was carried out in the same manner as Example 10, except that 23.42 g (0.158 mol) of 4-vinyl-phenyl boronic acid, 20.0 g (0.1055 mol) of 2-(2-chloro-phenyl)pyridine, 500□ of 1,4-dioxane, 27.54 g (0.474 mol, 3.3 equivalent) of fluoro-potassium, 1.69 g (0.0084 mol, 5.3 mol %) of t-butylphosphine [P( t-Bu)3)], and 2.6 g (0.0028 mol, 1.8 mol %) of palladium tris(dibenzylidene acetone) [Pd2(dba)3] were used. Finally, after the resulting solution was heated to reflux at 80° C. for 24 hours, the 2-(4′-vinyl-biphenyl-2-yl)pyridine was isolated. The yield was 50%.

Aufarbeitung

  1. temperatureFinally, after the resulting solution was heated

Quellen und Nachweise

ORD-Eintrag
ord-9d9f7d481a8745cfbc3d2b8eb30581ac
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110642B2

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