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

HRID 1457980Notes

Reaction equation

HRID 1457980 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 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 204 ml (1.6 mol) portion of ethyl acetoacetate and 138 ml (1.6 mol) of 1,2-dibromoethane were dissolved in 3 liters of N,N-dimethylformamide, and the solution was mixed with 460 g (3.3 mol) of potassium carbonate at room temperature and stirred at the same temperature for 2 days. After completion of the reaction, insoluble material was removed by filtration and then N,N-dimethylformamide was evaporated under a reduced pressure of 50 mmHg. The resulting residue was mixed with 1.5 liters of diethyl ether, washed with water (500 ml×3) and then dried over anhydrous sodium sulfate. By evaporating diethyl ether, 113.43 g (45%) of the title compound was obtained as an oily substance.

Workup

  1. customAfter completion of the reaction, insoluble material
  2. customwas removed by filtration
  3. customN,N-dimethylformamide was evaporated under a reduced pressure of 50 mmHg
  4. additionThe resulting residue was mixed with 1.5 liters of diethyl ether
  5. washwashed with water (500 ml×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customBy evaporating diethyl ether

Sources & evidence

ORD record
ord-dd1bf7cf9be54e28b2fd85b22389fccf
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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