N-bromobutanimide → Ethyl 2-acetyl-4-bromo-2-pentenoate

HRID 2398668Notes

Reaction equation

HRID 2398668 reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([C:4](=[CH:10][CH:11]([Br:13])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54249081Ethyl 2-acetyl-2-pentenoate

Product 1

HCID 54436818Ethyl 2-acetyl-4-bromo-2-pentenoateYield 98.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 8.06 g (0.047 mole) ethyl 2-acetyl-2-pentenoate and 8.43 g (0.047 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 15 minutes. The mixture was quickly cooled to room temperature, and the succinimide removed by filtration. Concentration of the solution in vacuo afforded 11.5 g (98%) of ethyl 2-acetyl-4-bromo-2-pentenoate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 minutes
  3. customthe succinimide removed by filtration

Sources & evidence

ORD record
ord-07e02a3875c849408b7705b5b1841f8b
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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