N-bromobutanimide → Ethyl 2-Methyl-3-furoate

HRID 2398649

Reaction equation

HRID 2398649 reaction equation
[C:1]([C:4](=[CH:10][CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:2][C:1]1[O:3][CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53941670Ethyl 2-acetylbut-2-enoate

Product 1

HCID 261900Ethyl 2-Methyl-3-furoateYield 24%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3.12 g (0.02 mole) ethyl 2-acetyl-2-butenoate and 3.56 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 19 hours. After cooling, the insoluble succinimide was removed by filtration and the solution concentrated by rotary evaporation. Distillation of the crude product gave 0.73 g (24%) of ethyl 2-methyl-3-furoate, bp 87°-9° C. (20 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 19 hours
  3. temperatureAfter cooling
  4. customthe insoluble succinimide was removed by filtration
  5. concentrationthe solution concentrated by rotary evaporation
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-9b92a50ab88542f7ab03d1dc7dab9998
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Linked notes

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