1-Bromo-3,5-bis(trifluoromethyl)benzene → HCID 22721470, compound

HRID 1581452Notes

Reaction equation

HRID 1581452 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.FC(F)(F)C1C=C(Br)C=C(C(F)(F)F)C=1.Cl[C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([CH3:43])[CH:41]=2)[N:36]=[C:35]([CH3:44])[CH:34]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C1COCC1>[CH3:44][C:35]1[CH:34]=[C:33]([C:5]2[CH:4]=[C:3]([C:2]([F:16])([F:15])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=2)[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([CH3:43])[CH:41]=2)[N:36]=1

Participants

7

Reactant 4

HCID 676021-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 812191,3-Bis(diphenylphosphino)propaneHCID 2342754-chloro-2,6-dimethylquinolineHCID 178506227HCID 178506227, compound

Product 1

HCID 22721470HCID 22721470, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

First, 3,5-bis(trifluoromethyl)phenylmagnesium bromide prepared from Mg and 3,5-bis(trifluoromethyl)bromobenzene was dropped into a THF solution of 4-chloro-2,6-dimethylquinoline (1 g) andNi(dpp)Cl2 (dpp: 1,3-bis(diphenylphosphino)propane) (0.1 g). Reactions were allowed to take place 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 2,6-dimethyl-4-[3,5-bis(trifluoromethyl)phenyl]quinoline (0.5 g).

Workup

  1. customfor 24 hours
  2. customat 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-f8702716f42b4b848dc31dd008987cff
Source dataset
uspto-grants-2004_05
Patent number
US06730418B2

Reaction notes

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