HCID 68465190, compound → 5-Bromo-7,8-dioxo-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester

HRID 502922Notes

Reaction equation

HRID 502922 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]2[C:11](OC)([O:14]C)[C:12](=[O:13])[CH:6]1[CH:7]=[C:8]2[Br:18])=[O:4]>FC(F)(F)C(O)=O.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]2[C:11](=[O:14])[C:12](=[O:13])[CH:6]1[CH:7]=[C:8]2[Br:18])=[O:4]

Participants

4

Reactant 1

HCID 68465190HCID 68465190, compound

Product 1

HCID 586095375-Bromo-7,8-dioxo-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3 g (9.4 mmol) of 5-bromo-8,8-dimethoxy-7-oxo-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester (J.O.C. (202), 67, 6493) are stirred in a mixture of 15 ml of trifluoroacetic acid and 1 ml of water for 12 hours at room temperature. Extraction is then carried out with dichloromethane against water. The organic phase is dried over sodium sulfate and yields, after removal of the solvent, the 5-bromo-7,8-dioxo-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester in the form of an orange-coloured oil and as a pure isomer.

Workup

  1. extractionExtraction
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customyields
  4. customafter removal of the solvent

Sources & evidence

ORD record
ord-2d61b46ef56048908fdaf2c41c64c622
Source dataset
uspto-grants-2010_08
Patent number
US07776888B2

Reaction notes

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