Reaktion #1253229

Reaktionsgleichung

3-bromo-2-methyl-6-methylsulfonylbenzaldehyde oxime

2-chloromethyl-3-chloropropene

sodium hypochlorite

NaOCl

sodium acetate

→

1-Bromo-2-methyl-3-[5,5-di(chloromethyl)-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzene

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAt room temperature
2. 2
   workup.ADDITIONwere added dropwise
3. 3
   SonstigeThe phases were separated
4. 4
   Waschenthe organic phase was washed three times with water
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated to dryness
7. 7
   SonstigeThe residue was chromatographed on silica gel using, as mobile phase, first cyclohexane

Vorschrift

At room temperature, 50 ml of sodium hypochlorite solution (which contained 3.8 g (51.4 mmol) of NaOCl, admixed with a spatula tip of sodium acetate) were added dropwise with stirring to a solution of 15 g (51.4 mmol) of 3-bromo-2-methyl-6-methylsulfonylbenzaldehyde oxime and 7.1 g (56.5 mmol) of 2-chloromethyl-3-chloropropene in 250 ml of methylene chloride. The reaction mixture was stirred at room temperature overnight. The phases were separated, and the organic phase was washed three times with water, dried and evaporated to dryness. The residue was chromatographed on silica gel using, as mobile phase, first cyclohexane, then cyclohexane/ethyl acetate 90:10 and finally cyclohexane/ethyl acetate 80:20. This gave 13.5 g of a white powder (63.3% of theory). M.p.: 144-145° C. The 1H-NMR spectrum found corresponds to the given structure.

Quelle