Reaktionsgleichung
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.Cl.Br[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>O.C1(P(CCCC[Pd-](Cl)Cl)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 4-(trifluoromethoxy)benzene boronic acid (2 g, 9.7 mmol), 4-bromopyridine hydrochloride (2.83 g, 14.5 mmol), diphenylphosphinobutylpalladium (II) dichloride (100 mg), dimethoxyethane (50 ml) and a 2M sodium carbonate solution (30 ml) were stirred at 85° C. for 2 hours. The solution was allowed to cool to ambient temperature diluted with water (100 ml), and extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over sodium sulphate. Removal of the solvents in vacuo gave an oil which was chromatographed on silica in 30% ethyl acetate/hexane giving the title compound as an oil (1.86 g, 80%). 1H NMR (250 MHz, CDCl3) δ 8.72-8.70 (2H, d, J=6.2 Hz), 7.69-7.63 (2H, d, J=9.6 Hz), 7.49-7.47 (2H, d, J=6.2 Hz), and 7.36-7.32 (2H, d, J=9.6 Hz). m/z (ES+) 240 (M+1).
Aufarbeitung
- extractionextracted with ethyl acetate (2×100 ml)
- dry with materialThe combined organic layers were dried over sodium sulphate
- customRemoval of the solvents in vacuo
- customgave an oil which
- customwas chromatographed on silica in 30% ethyl acetate/hexane giving the title compound as an oil (1.86 g, 80%)
Quellen und Nachweise
- ORD-Eintrag
- ord-cd14e6b7c3c444f3a6ac9cdadea5b074
- Quelldatensatz
- uspto-grants-2000_05
- Patentnummer
- US06060469
Verknüpfte Notizen
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