Reaktion #1668637

Reaktionsgleichung

Magnesium

3,5-bis (trifluoromethyl)phenylbromide

4-chloro-2,6-dimethylquinoline

3,5-bis(trifluoromethyl)phenylmagnesiumbromide

→

3,5-bis (trifluoromethyl)phenylmagnesiumbromide

4-(3,5-bis(trifluoromethyl)phenyl)-2,6-dimethylquinoline

Lösungsmittel

THF

Water

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas dropped
2. 2
   workup.ADDITIONdispersed
3. 3
   workup.ADDITIONabove was dropped to the suspension
4. 4
   workup.STIRRINGthe resulting solution was stirred for 4 days at room temperature
5. 5
   Filtrationwere filtered
6. 6
   Extraktionextraction
7. 7
   Sonstigethe solvent was removed under a reduced pressure
8. 8
   SonstigeThe residue was purified through a silica gel column (hexane/ethyl acetate=3/2)

Vorschrift

Magnesium (1.60 g) was added to THF (60 ml) in a nitrogen atmosphere and 3,5-bis (trifluoromethyl)phenylbromide (17.58 g) was dropped. The resulting mixture was stirred for 30 minutes at room temperature and a THF solution of 3,5-bis (trifluoromethyl)phenylmagnesiumbromide was prepared. In a nitrogen atmosphere, 4-chloro-2,6-dimethylquinoline (2.88 g) and Ni(dpp)Cl2 (500 mg) were added to THF (30 ml) and dispersed. The THF solution of 3,5-bis(trifluoromethyl)phenylmagnesiumbromide prepared as above was dropped to the suspension and the resulting solution was stirred for 4 days at room temperature. Water was poured into the reaction solution, impurities were filtered, and extraction was performed using AcOEt (ethyl acetate). A drying process was applied using Na2SO4 and the solvent was removed under a reduced pressure. The residue was purified through a silica gel column (hexane/ethyl acetate=3/2) to obtain 4-(3,5-bis(trifluoromethyl)phenyl)-2,6-dimethylquinoline (4.40 g) represented by the following chemical formula (49).

Quelle