N-bromobutanimide → 3-[3-Bromo-4-(bromomethyl)phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

HRID 386732Notes

Reaction equation

HRID 386732 reaction equation
[Br: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>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[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:5]=[CH:6][C:7]=1[CH2:8][Br:26]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86643372HCID 86643372, compound

Product 1

HCID 866433713-[3-Bromo-4-(bromomethyl)phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazoleYield 71%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3-(3-bromo-4-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (1.2 g), N-bromosuccinimide (0.54 g) and 2,2′-azobisisobutylonitrile (0.05 g) in dichloroethane (20 mL) was heated to reflux for 3 hours. The solvent was distilled off under reduced pressure, the residue was diluted with t-butylmethylether, and the solution was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to yield 3-[3-bromo-4-(bromomethyl)-phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (1.0 g).

Workup

  1. temperatureto reflux for 3 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe residue was diluted with t-butylmethylether
  4. washthe solution was washed with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a544bbb1ab5a478e90df31965eca2dcc
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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