N-bromobutanimide → HCID 86643370, compound

HRID 386727Notes

Reaction equation

HRID 386727 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:21]([F:24])([F:23])[F:22])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Br:25]N1C(=O)CCC1=O>ClC(Cl)C>[Br:25][CH2:20][C:17]1[CH:16]=[CH:15][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:21]([F:22])([F:24])[F:23])[O:13][N:12]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58223543HCID 58223543, compound

Product 1

HCID 86643370HCID 86643370, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 5-(3,5-dichlorophenyl)-3-(4-methylphenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (5.3 g), N-bromosuccinimide (3.7 g) and 2,2′-azobisisobutylonitrile (0.1 g) in dichloroethane (40 mL) was heated to reflux for 3 hours. After 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 then purified by silica gel chromatography to obtain 3-[4-(bromomethyl)phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (2.5 g).

Workup

  1. temperatureto reflux for 3 hours
  2. distillationAfter the 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 then purified by silica gel chromatography

Sources & evidence

ORD record
ord-3289cf93411b497c836d7a8397ccd1fe
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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