[CH3:1][C:2]1[C:11](Cl)=[C:10]([CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:43][C:44]([F:58])([F:57])[C:45]1[CH:46]=[C:47]([Mg]Br)[CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1.FC(F)(F)C1C=C(Br)C=C(C(F)(F)F)C=1>O.C1COCC1>[CH3:1][C:2]1[C:11]([C:47]2[CH:48]=[C:49]([C:51]([F:54])([F:52])[F:53])[CH:50]=[C:45]([C:44]([F:43])([F:58])[F:57])[CH:46]=2)=[C:10]([CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1To a THF solution of the obtained 2,4-dimethyl-3-chloroquinoline (0.65 g) and Ni(dpp)Cl2 (dpp: 1,3-bis(diphenylphosphino)propane) (0.1 g), 3,5-bis (trifluoromethyl)phenylmagnesium bromide prepared from Mg and 3,5-bis(trifluoromethyl)bromobenzene was dropped and the reaction solution was allowed to react for 24 hours at room temperature. Water was added to the reaction solution and the organic layer was extracted using CHCl3. The solvent was removed under reduced pressure and the residue was purified through column chromatography to obtain 2,4-dimethyl-3-[3,5-bis(trifluoromethyl)phenyl]quinoline.
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