Hydrogen Peroxide → HCID 86663663, compound

HRID 1193221Notes

Reaction equation

HRID 1193221 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:19])=[C:6]([CH:8]=[C:9]2[C:13]([CH3:15])([CH3:14])[O:12][C:11]([CH3:17])([CH3:16])[C:10]2=[O:18])[CH:7]=1.[OH:20]O.[OH-].[Li+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:19])=[C:6]([CH:8]2[C:9]3([C:10](=[O:18])[C:11]([CH3:17])([CH3:16])[O:12][C:13]3([CH3:14])[CH3:15])[O:20]2)[CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 66823581HCID 66823581, compound

Product 1

HCID 86663663HCID 86663663, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 4-[1-(5-bromo-2-iodophenyl)methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (1.18 g, 2.73 mmol) in methanol (50 ml) at 35 ° C. is added 50% aqueous hydrogen peroxide solution (0.31 ml, 5.46 mmol), followed immediately by 2M aqueous lithium hydroxide (0.34 ml, 0.68 mmol). This mixture is stirred at 35 ° C. for 3 hours, then quenched with saturated aqueous sodium metabisulfite and extracted with dichloromethane. The organic phase is separated, and the aqueous phase extracted again with dichloromethane. All organics are combined then evaporated under reduced pressure to afford 2-(5-bromo-2-iodophenyl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one as an oil which is used directly in the next step.

Workup

  1. customquenched with saturated aqueous sodium metabisulfite
  2. extractionextracted with dichloromethane
  3. customThe organic phase is separated
  4. extractionthe aqueous phase extracted again with dichloromethane
  5. customAll organics are combined then evaporated under reduced pressure

Sources & evidence

ORD record
ord-cabf9f184f224487b7c9cc60f776bded
Source dataset
uspto-grants-2014_03
Patent number
US08680299B2

Reaction notes

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