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

HRID 1166046

Reaktionsgleichung

Reaktionsgleichung von HRID 1166046
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]

Komponenten

8

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bb837d07e9b04a718187ce79942be239
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613719B1

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