Reaktionsgleichung
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH3:11][PH:12](=[O:14])[CH3:13].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[CH3:11][P:12]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1)([CH3:13])=[O:14]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a solution of 1-iodo-3-nitrobenzene (2.4 g, 9.6 mmol) in dry 1,4-dioxane (24 ml) in a pressure bottle under nitrogen at room temperature was added dimethylphosphine oxide [WO 2005/009348] (1.5 g, 19.2 mmol), Pd2(dba)3 (0.44 g, 0.48 mmol), Xantphos (0.56 g, 0.96 mmol) and cesium cabonate (4.38 g, 13.5 mmol). The mixture was degassed by bubbling nitrogen into the solution for 10 min. The pressure bottle was closed and heated at 90° C. for 3 h. The solvent was removed under reduced pressure and the residue was purified via Biotage (linear gradient 0-20%, methanol/ethyl acetate; 25M column) to afford title compound 286 as a brown solid (1.52 g, 7.63 mmol, 79%). MS (m/z): 200.1 (M+H).
Aufarbeitung
- customThe mixture was degassed
- customby bubbling nitrogen into the solution for 10 min
- customThe pressure bottle was closed
- customThe solvent was removed under reduced pressure
- customthe residue was purified via Biotage (linear gradient 0-20%, methanol/ethyl acetate; 25M column)
Quellen und Nachweise
- ORD-Eintrag
- ord-dec26ec910c14b168511843357aa73d6
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08759522B2
Verknüpfte Notizen
Wird geladen…