Chlorine → 1-Bromo-2-methyl-3-[5-(4-chlorobutyl)-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzene

HRID 1166046

Reaction equation

HRID 1166046 reaction equation
Cl[O-].[Na+].ClCl.C([O-])(=O)C.[Na+].[Br:11][C:12]1[C:13]([CH3:25])=[C:14]([C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=1)[CH:15]=[N:16][OH:17].[Cl:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32]>C(Cl)Cl.O>[Br:11][C:12]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[C:14]([C:15]2[CH2:32][CH:31]([CH2:30][CH2:29][CH2:28][CH2:27][Cl:26])[O:17][N:16]=2)[C:13]=1[CH3:25]

Participants

8

Reactant 5

HCID 24526ChlorineHCID 702336-Chloro-1-hexeneHCID 517045Sodium AcetateHCID 23665760Sodium HypochloriteHCID 734619443-Bromo-2-methyl-6-methylsulfonylbenzaldoxime

Product 1

HCID 229969731-Bromo-2-methyl-3-[5-(4-chlorobutyl)-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

At room temperature, 50 ml of sodium hypochlorite solution (12.5% of active chlorine, admixed with a spatula tip of sodium acetate) were added dropwise with vigorous stirring to a solution of 15 g (51.4 mmol) of 3-bromo-2-methyl-6-methylsulfonylbenzaldehyde oxime and 6.7 g (56.5 mmol) of 6-chlorohexene in 200 ml of methylene chloride. The reaction mixture was stirred at room temperature overnight. The reaction mixture was then stirred into 300 ml of water. The organic phase was washed three times with water, dried and concentrated to dryness. This gave 19.3 g of a viscous yellow oil (92.4% of theory). The 1H-NMR spectrum corresponds to the given structure.

Workup

  1. customAt room temperature
  2. additionwere added dropwise
  3. washThe organic phase was washed three times with water
  4. customdried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bb837d07e9b04a718187ce79942be239
Source dataset
uspto-grants-2003_09
Patent number
US06613719B1

Linked notes

Loading…