Dichloromethane → Methyl 2-chloro-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate

HRID 2167423Notes

Reaction equation

HRID 2167423 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[N:13][OH:14])=[C:10]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].ClCCl.[C:22]([O-])(=O)[CH3:23].[Na+].Cl[O-].[Na+]>C=C>[Cl:1][C:2]1[C:11]([C:12]2[CH2:23][CH2:22][O:14][N:13]=2)=[C:10]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 23665760Sodium HypochloriteHCID 86584467Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate

Product 1

HCID 22114925Methyl 2-chloro-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate

Reagents, catalysts & solvents 1

HCID 6325EthyleneSolvent3×

Procedure

Ethylene was passed for 30 minutes at 15-20° C. into a solution of 158.0 g (0.54 mol) of methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate and 1 l of dichloromethane. After 1.6 g of sodium acetate had been added, 454 ml of sodium hypochlorite solution were added dropwise at 10° C. while simultaneously passing in ethylene. Ethylene was subsequently passed in at 10° C. for a further 15 minutes. After the mixture had been stirred for 12 hours, the phases were separated, and the organic phase was washed with water, dried and concentrated. This gave 156.5 g (90% of theory) of methyl 2-chloro-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate.

Workup

  1. customthe phases were separated
  2. washthe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0c51dc8e8624f069dfdbd12e2ffed24
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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