Azobisisobutyronitrile → HCID 86685042, compound

HRID 532139Notes

Reaction equation

HRID 532139 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:25].C1C(=O)N([Br:33])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:15])([F:14])[F:16])[O:10][N:9]=2)=[CH:4][C:3]=1[CH2:25][Br:33]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Product 1

HCID 86685042HCID 86685042, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (100 mg, 0.221 mmol), NBS (62.8 mg, 0.35 mmol) and AIBN (cat.) in 1,2-dichloroethane (10 mL) was refluxed for 3.5 h and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel to give crude 3-(4-bromo-3-(bromomethyl)phenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (50 mg, yield 42%) as an oil.

Workup

  1. temperaturewas refluxed for 3.5 h
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-566fd493bbfd451a87a66b91b4ba5f75
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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