1-Bromo-3,5-bis(trifluoromethyl)benzene → HCID 22721472, compound

HRID 1581451Notes

Reaction equation

HRID 1581451 reaction equation
[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]=1

Participants

7

Reactant 4

HCID 676021-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 812191,3-Bis(diphenylphosphino)propaneHCID 110846922,4-dimethyl-3-chloroquinolineHCID 178506227HCID 178506227, compound

Product 1

HCID 22721472HCID 22721472, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 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.

Workup

  1. additionwas dropped
  2. customto react for 24 hours at room temperature
  3. extractionthe organic layer was extracted
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified through column chromatography

Sources & evidence

ORD record
ord-ea8b7a32c1914b7a8f7b9eeebab843de
Source dataset
uspto-grants-2004_05
Patent number
US06730418B2

Reaction notes

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