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

HRID 964032Notes

Reaction equation

HRID 964032 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].Br[CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:3]([C:2]1([C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH2:12][CH2:11]1)(=[O:4])[CH3:5]

Participants

5

Reactant 3

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

Product 1

HCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 10.4 g of ethyl acetoacetate were added 15 g of 1,2-dibromoethane, 23 g of potassium carbonate, and 150 ml of N,N-dimethylformamide (DMF), and the mixture was stirred at room temperature for 2 days. Any insoluble matter was removed by filtration, and the filtrate was evaporated to dryness under reduced pressure. To the residue was added water, and the mixture was extracted with chloroform. The chloroform extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting pale yellow oily substance was subjected to distillation under reduced pressure to obtain 7.5 g of ethyl 1-acetyl-1-cyclopropanecarboxylate having a boiling point of 70° to 71° C./2 to 3 mmHg.

Workup

  1. customAny insoluble matter was removed by filtration
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. additionTo the residue was added water
  4. extractionthe mixture was extracted with chloroform
  5. extractionThe chloroform extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. distillationThe resulting pale yellow oily substance was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-48c1d8647b114df3ba5698dc4a6d677a
Source dataset
uspto-grants-1998_06
Patent number
US05767127

Reaction notes

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