Ethylene → 3-(3,6-Dibromo-2-methylphenyl)-4,5-dihydroisoxazole

HRID 394839Notes

Reaction equation

HRID 394839 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:8]([Br:11])=[CH:9][CH:10]=1)[CH:5]=[N:6][OH:7].[CH2:13]=[CH2:14].[O-]Cl.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:5]2[CH2:14][CH2:13][O:7][N:6]=2)[C:8]([Br:11])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6325EthyleneHCID 23665760Sodium HypochloriteHCID 865861873,6-Dibromo-2-methylbenzaldoxime

Product 1

HCID 121004313-(3,6-Dibromo-2-methylphenyl)-4,5-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

68 g (0.23 mol) of 3,6-dibromo-2-methylbenzaldoxime are dissolved in 750 ml of methylene chloride in a pressure container. 20 g of ethylene are applied, and 620 g of a 12.5% strength solution of NaOCl are then pumped in at room temperature, and the mixture is stirred overnight. The pressure vessel is vented, and the organic phase is then separated off, washed once with 250 ml of water and dried, and the solvent is removed under reduced pressure. This gives 77 g of product (95% pure) (99% of theory).

Workup

  1. customare then pumped in at room temperature
  2. customthe organic phase is then separated off
  3. washwashed once with 250 ml of water
  4. customdried
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-1b239b927d31454da5022453a46df9d6
Source dataset
uspto-grants-2003_08
Patent number
US06603017B2

Reaction notes

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