Water → HCID 4313443, compound

HRID 2122104Notes

Reaction equation

HRID 2122104 reaction equation
C[N+]1([O-])CC[O:5]CC1.Br[CH:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12].O>CS(C)=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:10](=[O:5])[C:11]([O:13][CH3:14])=[O:12])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

Product 1

HCID 4313443HCID 4313443, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
22.5 °C

Procedure

97.2 g of a 75% strength aqueous N-methylmorpholine N-oxide solution were added with ice-cooling to a solution of 100 g (0.38 mol) of the compound of Example 1 in 400 ml of dimethyl sulfoxide (DMSO). After the mixture had been stirred for 24 hours at 20 to 25° C., it was poured into water and extracted with methyl tert-butyl ether (MtBE). After the organic phases had been dried, stripped from the solvent and chromatographed on silica gel (cyclohexane/MtBE [3:1]), 69 g of the title compound was obtained.

Workup

  1. extractionextracted with methyl tert-butyl ether (MtBE)
  2. customAfter the organic phases had been dried
  3. customchromatographed on silica gel (cyclohexane/MtBE [3:1])

Sources & evidence

ORD record
ord-93aee7b7907a4e18a83dbb438d45307f
Source dataset
uspto-grants-2004_02
Patent number
US06696607B2

Reaction notes

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