1,2-Dichloroethane → HCID 86761701, compound

HRID 1880248Notes

Reaction equation

HRID 1880248 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2([C:25]([F:28])([F:27])[F:26])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Br[N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].N([C:44]([CH3:48])([CH3:47])C#N)=NC(C)(C)C#N.O.Cl[CH2:51]CCl>>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2([C:25]([F:28])([F:26])[F:27])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:30]4[C:34](=[O:35])[C:33]5=[CH:51][CH:48]=[CH:44][CH:47]=[C:32]5[C:31]4=[O:36])=[C:19]([Cl:24])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:7]=1

Participants

6

Reactant 5

HCID 111,2-Dichloroethane2×HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 86761700HCID 86761700, compound

Product 1

HCID 86761701HCID 86761701, compound

Procedure

To a solution of 3.56 g of 5-[3-bromo-5-(trifluoromethyl)phenyl]-3-(3-chloro-4-methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 15 mL of 1,2-dichloroethane, 1.43 g of N-bromosuccinimide and 0.096 g of α,α′-azobisisobutyronitrile were added and the resultant mixture was stirred while heating the reaction mixture to reflux for 3 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and 50 mL of 1,2-dichloroethane was added to the reaction mixture. Subsequently, the resultant mixture was washed with water (30 mL×1) and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in 7 mL of an N,N-dimethylformamide solution, and 1.35 g of a phthalimide potassium salt was added to the resultant solution, followed by stirring the resultant mixture at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was charged into 30 mL of water and the resultant reaction mixture was extracted with ethyl acetate (25 mL×2). The organic phase was dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order, and the solvent was distilled off under reduced pressure to obtain 5.26 g of a crude objective substance as a light yellow resinoid. This substance was used in the next process as it was without being further purified.

Workup

  1. temperaturewhile heating the reaction mixture
  2. temperatureto reflux for 3 hours
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. washSubsequently, the resultant mixture was washed with water (30 mL×1)
  6. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThe resultant residue was dissolved in 7 mL of an N,N-dimethylformamide solution
  9. addition1.35 g of a phthalimide potassium salt was added to the resultant solution
  10. customAfter the completion of the reaction
  11. customthe resultant reaction mixture
  12. extractionwas extracted with ethyl acetate (25 mL×2)
  13. dry with materialdried over saturated saline and anhydrous magnesium sulfate in this order
  14. distillationthe solvent was distilled off under reduced pressure
  15. customto obtain 5.26 g of a crude objective substance as a light yellow resinoid

Sources & evidence

ORD record
ord-42ef863cffba4c8487c7f0266a81beeb
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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