N-bromobutanimide → HCID 12452845, compound

HRID 2398662Notes

Reaction equation

HRID 2398662 reaction equation
[C:1]([C:6](=[CH:12][CH2:13][CH3:14])[C:7](=[O:11])[CH2:8][CH2:9][CH3:10])([O:3][CH2:4][CH3:5])=[O:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:14][C:13]1[O:11][C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54517126HCID 54517126, compound

Product 1

HCID 12452845HCID 12452845, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3.97 g (0.02 mole) 5-carboethoxy-5-octen-4-one and 3.56 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 by rotary evaporation. Distillation of the crude product gave 3.35 g (85%) of ethyl 5-methyl-2-propyl- 3-furoate, bp 104°-107° C. (9.5 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 by rotary evaporation
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-a511f2cf347144c4bf46738aecd2fce6
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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