1,2-Dibromoethane → Ethyl 1-acetylcyclopropane-1-carboxylate

HRID 1366511Notes

Reaction equation

HRID 1366511 reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18]Br>CN(C=O)C>[C:2]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:18][CH2:17]1)(=[O:1])[CH3:9]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 8868Ethyl AcetoacetateHCID 11430Potassium Carbonate

Product 1

HCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-oxobutanoate (10.0 g, 76.84 mmol) in DMF (150 mL) was added potassium carbonate (22.30 g, 161.3 mmol) and 1,2-dibromoethane (6.62 mL, 76.82 mmol). The mixture was stirred for 2 days, and then filtered. The solution was diluted with water (300 mL), and extracted with Et2O (2×200 mL). The combined organic phase was washed with a fresh portion of water (100 mL), dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was subjected to vacuum distillation at ca. 10 mbar, and the fraction boiling at 100° C. was collected to give ethyl 1-acetylcyclopropanecarboxylate (7.6482 g, 64%) as a colorless oil.

Workup

  1. filtrationfiltered
  2. additionThe solution was diluted with water (300 mL)
  3. extractionextracted with Et2O (2×200 mL)
  4. washThe combined organic phase was washed with a fresh portion of water (100 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. distillationThe residue was subjected to vacuum distillation at ca. 10 mbar
  9. customthe fraction boiling at 100° C. was collected

Sources & evidence

ORD record
ord-e426b7e69b8948cfbe8acf1517ab7811
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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