N-bromobutanimide → HCID 12452842, compound

HRID 2398656Notes

Reaction equation

HRID 2398656 reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[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][C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 30175142-Nonenoic acid, 2-acetyl-, ethyl ester

Product 1

HCID 12452842HCID 12452842, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4.33 g (0.02 mole) ethyl 2-acetyl-2-nonenoate and 3.57 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 12 hours. After cooling, the succinimide was removed by filtration and the solution concentrated in vacuo. Distillation of the crude product gave 3.09 g (69%) of ethyl 2-methyl-5-pentyl-3-furoate, bp 115°-119° C. (1.3 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. concentrationthe solution concentrated in vacuo
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-2f17ab33e8794a20b8624152d4c6845e
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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