N-bromobutanimide → HCID 86643374, compound

HRID 386736Notes

Reaction equation

HRID 386736 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Br:28]N1C(=O)CCC1=O>ClC(Cl)C>[Br:28][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=2)=[CH:15][C:16]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59355619HCID 59355619, compound

Product 1

HCID 86643374HCID 86643374, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 5-(3,5-dichlorophenyl)-3-(4-methyl-3-nitrophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (1.9 g), N-bromosuccinimide (0.9 g) and 2,2′-azobisisobutylonitrile (0.1 g) in dichloroethane was heated to reflux for 3 hours. The reaction solution was washed with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then purified by silica gel chromatography to yield 3-[4-(bromomethyl)-3-nitrophenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (1.2 g).

Workup

  1. temperatureto reflux for 3 hours
  2. washThe reaction solution was washed with water
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-b4ab33cb41ce41e3922cb7cafc46432d
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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