Water → HCID 53980998, compound

HRID 477584Notes

Reaction equation

HRID 477584 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C@@:6]12[CH2:13][CH2:12][C@@H:11]1[CH2:10][CH2:9][C:8](Br)([Br:14])[C:7]2=[O:16])[CH3:2].C(=O)([O-])[O-].[Li+].[Li+].O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C@@:6]12[CH2:13][CH2:12][C@@H:11]1[CH2:10][CH:9]=[C:8]([Br:14])[C:7]2=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11125Lithium CarbonateHCID 54066689HCID 54066689, compound

Product 1

HCID 53980998HCID 53980998, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

cis-3,3-Dibromo-2-oxobicyclo[4.2.0]octane-1-acetic acid ethyl ester (14.16 g) lithium bromide (4.88 g, 56.21 mmol), and lithium carbonate (2.98 g, 14.4 mmol) were dissolved in 47.3 mL of DMF under nitrogen and heated to 100° C. for 5 minutes. The reaction mixture was then poured into 500 mL of water and extracted with 4×100 mL of toluene. The organic phase washed with 4×100 mL of water, dried over MgSO4, and concentrated in vacuo affording 8.86 g (80%) of product.

Workup

  1. extractionextracted with 4×100 mL of toluene
  2. washThe organic phase washed with 4×100 mL of water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-441e8ff0f03f4364abf6b316d0874d73
Source dataset
uspto-grants-1989_12
Patent number
US04888431

Reaction notes

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