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

HRID 1581455Notes

Reaction equation

HRID 1581455 reaction equation
[Mg].[F:2][C:3]([F:16])([F:15])[C:4]1[CH:5]=[C:6](Br)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([CH3:28])[CH:26]=2)[N:21]=[C:20]([CH3:29])[CH:19]=1.[F:30][C:31]([F:45])([F:44])[C:32]1[CH:33]=[C:34]([Mg:42][Br:43])[CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1>O.C1COCC1>[F:45][C:31]([F:30])([F:44])[C:32]1[CH:33]=[C:34]([Mg:42][Br:43])[CH:35]=[C:36]([C:38]([F:40])([F:41])[F:39])[CH:37]=1.[F:2][C:3]([F:16])([F:15])[C:4]1[CH:5]=[C:6]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([CH3:28])[CH:26]=3)[N:21]=[C:20]([CH3:29])[CH:19]=2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1

Participants

8

Reactant 4

HCID 676021-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 2342754-chloro-2,6-dimethylquinolineHCID 5462224MagnesiumHCID 178506227HCID 178506227, compound

Product 2

HCID 22721470HCID 22721470, compoundHCID 178506227HCID 178506227, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

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).

Workup

  1. additionwas dropped
  2. additiondispersed
  3. additionabove was dropped to the suspension
  4. stirringthe resulting solution was stirred for 4 days at room temperature
  5. filtrationwere filtered
  6. extractionextraction
  7. customthe solvent was removed under a reduced pressure
  8. customThe residue was purified through a silica gel column (hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-f0919f80027b40ec970c1f1b4439c43b
Source dataset
uspto-grants-2004_05
Patent number
US06730418B2

Reaction notes

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