Reaktionsgleichung
[Br-].[Mg+2].[Br-].Cl[C:5]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[C:9]([CH3:19])[C:6]=1[C:7]#[N:8].[OH-].[NH4+].[OH-].[Na+].[CH2:24]1COCC1>[Cu](Br)Br>[CH3:24][C:5]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[C:9]([CH3:19])[C:6]=1[C:7]#[N:8]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Copper bromide (2.56 g, 17.49 mmol) was suspended in 20 mL of anhydrous THF, dropwisely added with magnesium bromide (3.0M ether, 11.66 mL, 34.99 mmol) at −78° C. and stirred for about 20 minutes. A 10 mL of anhydrous TNF was dropwisely added with a solution, wherein 2 chloro-6-phenyl-4-methyl-nicotinonitrile was dissolved, at the above temperature and then stirred for about 1 hour at room temperature. The mixture was added with a saturated solution of ammonium hydroxide and adjusted its pH to 10 with 1 N NaOH. Then, it was extracted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. A silica gel column chromatography (5% EtOAc/Hexane) was performed on the resulting residue and 550 mg (55%) of 2,4-dimethyl-6-phenyl-nicotinonitrile was obtained in white solid.
Aufarbeitung
- dissolutionwas dissolved, at the above temperature
- stirringstirred for about 1 hour at room temperature
- extractionThen, it was extracted with ethyl acetate
- dry with materialdried with anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-5c6b5aac4ccc4e76b5d1180c1520fc4d
- Quelldatensatz
- uspto-grants-2009_10
- Patentnummer
- US07601736B2
Verknüpfte Notizen
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