N-bromobutanimide → HCID 12452841, compound

HRID 2398654Notes

Reaction equation

HRID 2398654 reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH:12]([C:11]1[O:3][C:1]([CH3:2])=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:10]=1)([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53685969HCID 53685969, compound

Product 1

HCID 12452841HCID 12452841, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3.97 g (0.02 mole) ethyl 2-acetyl-5-methyl-2-hexenoate and 3.55 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 2.5 hours. After cooling, the succinimide was removed by filtration and the solution concentrated by rotary evaporation. Distillation of the crude product gave 3.33 g (85% ) of ethyl 5-isopropyl-2-methyl-3-furoate, bp 112°-114° C. (11 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. concentrationthe solution concentrated by rotary evaporation
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-0728c37e81da434bb73d2191524a42e2
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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