Water → 5-[3,5-Bis(trifluoromethyl)phenyl]-3-[4-(1-bromoethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole

HRID 1880239Notes

Reaction equation

HRID 1880239 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C:13]2([C:26]([F:29])([F:28])[F:27])[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Br:32]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>ClCCCl>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([C:13]2([C:26]([F:27])([F:28])[F:29])[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([CH:24]([Br:32])[CH3:25])=[CH:22][CH:23]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 867616915-[3,5-Bis(trifluoromethyl)phenyl]-3-(4-ethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Product 1

HCID 867616925-[3,5-Bis(trifluoromethyl)phenyl]-3-[4-(1-bromoethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3.00 g of 5-[3,5-bis(trifluoromethyl)phenyl]-3-(4-ethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 15 mL of 1,2-dichloroethane, 1.29 g of N-bromosuccinimide and 0.10 g of α,α′-azobisisobutyronitrile were added and the resultant mixture was stirred at 75° C. for 3 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and then 10 mL of water was added to the reaction mixture. The resultant mixture was extracted with chloroform (20 mL×1). The organic phase was washed with water (10 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. To the resultant residue, hexane was added and a deposited crystal was filtered off to obtain 3.01 g of the objective substance as a white crystal.

Workup

  1. customAfter the completion of the reaction
  2. waitthe reaction mixture was left
  3. extractionThe resultant mixture was extracted with chloroform (20 mL×1)
  4. washThe organic phase was washed with water (10 mL×1)
  5. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the resultant residue, hexane was added
  8. filtrationa deposited crystal was filtered off
  9. customto obtain 3.01 g of the objective substance as a white crystal

Sources & evidence

ORD record
ord-4a46ae952820425795b91b41ddfbebea
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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