N-bromobutanimide → 3-(4-Bromomethyl-3-chlorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 885799Notes

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

Participants

Conditions

Temperature: 70 °C

Procedure

In a solution of 13.7 g of 3-(3-chloro-4-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole in 100 mL of 1,2-dichloroethane, 6.6 g of N-bromosuccinimide and 0.1 g of α,α′-azobisisobutyronitrile were added, and stirred at 70° C. for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, washed with water (70 mL×2), and dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and then the solvent was distilled off under reduced pressure. The residual solid was washed with diisopropyl ether to obtain 12.1 g of the aimed product as pale yellow crystal.

Workup

customAfter the completion of the reaction
waitthe reaction mixture was left
temperaturecooled to room temperature
washwashed with water (70 mL×2)
dry with materialdried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order
distillationthe solvent was distilled off under reduced pressure
washThe residual solid was washed with diisopropyl ether

Sources & evidence

ORD record: ord-1d9d6624151c44f4bb6363a3dbc1af4e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242283B2

Reaction notes

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