3-Chloro-2-chloromethyl-1-propene → HCID 22996975, compound

HRID 1166047Notes

Reaction equation

HRID 1166047 reaction equation
Cl[O-].[Na+].C([O-])(=O)C.[Na+].[Br:9][C:10]1[C:11]([CH3:23])=[C:12]([C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][CH:18]=1)[CH:13]=[N:14][OH:15].[Cl:24][CH2:25][C:26]([CH2:28][Cl:29])=[CH2:27]>C(Cl)Cl>[Br:9][C:10]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[C:12]([C:13]2[CH2:27][C:26]([CH2:28][Cl:29])([CH2:25][Cl:24])[O:15][N:14]=2)[C:11]=1[CH3:23]

Participants

6

Reactant 4

HCID 158593-Chloro-2-chloromethyl-1-propeneHCID 517045Sodium AcetateHCID 23665760Sodium Hypochlorite2×HCID 734619443-Bromo-2-methyl-6-methylsulfonylbenzaldoxime

Product 1

HCID 22996975HCID 22996975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customAt room temperature
  2. additionwere added dropwise
  3. customThe phases were separated
  4. washthe organic phase was washed three times with water
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel using, as mobile phase, first cyclohexane

Sources & evidence

ORD record
ord-3f0e7ff0d509431c83ddf9bbc65f2641
Source dataset
uspto-grants-2003_09
Patent number
US06613719B1

Reaction notes

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