Hydrogen Peroxide → HCID 86663665, compound

HRID 1193227Notes

Reaction equation

HRID 1193227 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH:15]=[C:16]1[C:20]([CH3:22])([CH3:21])[O:19][C:18]([CH3:24])([CH3:23])[C:17]1=[O:25].[OH:26]O.[OH-].[Li+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[CH:15]1[C:16]2([C:17](=[O:25])[C:18]([CH3:24])([CH3:23])[O:19][C:20]2([CH3:21])[CH3:22])[O:26]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 66823613HCID 66823613, compound

Product 1

HCID 86663665HCID 86663665, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 4-[1-(4-bromo-4′-chlorobiphenyl-3-yl)-methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (3.40 g, 9.03 mmol) in methanol (140 ml) at 35° C. is added 50% aqueous hydrogen peroxide (1.04 ml, 15.60 mmol), immediately followed by 2M aqueous lithium hydroxide (1.15 ml, 2.30 mmol). The reaction mixture is stirred for a further 45 minutes at 35° C., then allowed to cool to room temperature and quenched with saturated sodium metabisulfite. After extracting the product into diethyl ether (×3) the organic phase is separated, washed with additional water, then dried over magnesium sulfate. After filtration the filtrate is concentrated in vacuo to afford 2-(4-bromo-4′-chlorobiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one (3.0 g) as a yellow solid. This material was of sufficient purity to use directly in the next step.

Workup

  1. temperatureto cool to room temperature
  2. customquenched with saturated sodium metabisulfite
  3. extractionAfter extracting the product into diethyl ether (×3) the organic phase
  4. customis separated
  5. washwashed with additional water
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration the filtrate
  8. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-a7bdc9691f124d40bfccd655e58d8f88
Source dataset
uspto-grants-2014_03
Patent number
US08680299B2

Reaction notes

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