Azobisisobutyronitrile → 3-(4-Bromomethyl-3-chlorophenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

HRID 1880234Notes

Reaction equation

HRID 1880234 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:27]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClCCCl>[Br:27][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=3)([C:14]([F:17])([F:15])[F:16])[O:11][N:10]=2)=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 867616883-(3-Chloro-4-methylphenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Product 1

HCID 867616893-(4-Bromomethyl-3-chlorophenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 26.2 g of 3-(3-chloro-4-methylphenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 200 mL of 1,2-dichloroethane, 12.1 g of N-bromosuccinimide and 0.81 g of α,α′-azobisisobutyronitrile were added and the resultant reaction mixture was stirred at 80° C. for 3 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and was washed with water (70 mL×2). Subsequently, the washed reaction mixture was dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure to obtain 34.1 g of a crude objective substance as a brown oily substance. This substance was used in the next process as it was without being further purified.

Workup

  1. customthe resultant reaction mixture
  2. customAfter the completion of the reaction
  3. waitthe reaction mixture was left
  4. temperatureto be cooled down to room temperature
  5. washwas washed with water (70 mL×2)
  6. customSubsequently, the washed reaction mixture
  7. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  8. distillationthe solvent was distilled off under reduced pressure
  9. customto obtain 34.1 g of a crude objective substance as a brown oily substance

Sources & evidence

ORD record
ord-c56697c8f22f45f2907fb67a38945b73
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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