Homoallyl bromide → N-(3-Buten-1-yl)phthalimide

HRID 1070754Notes

Reaction equation

HRID 1070754 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[K].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12>CC(CC)=O>[CH2:2]([N:11]1[C:7](=[O:17])[C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]1=[O:12])[CH2:3][CH:4]=[CH2:5]

Participants

4

Reactant 2

HCID 21241Homoallyl bromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 339432N-(3-Buten-1-yl)phthalimide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

50 g (370 mmol) 4-bromo-1-butene and 68.5 g (370 mmol) phthalimide potassium salt are suspended in 800 ml ethyl methyl ketone and heated under reflux for 14 hours. After cooling, the mixture is filtrated and the filtrate is concentrated under vacuum. The residue is taken up in acetic acid ethyl ester and washed with water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum: yield 50 g (67%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 14 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtrated
  5. concentrationthe filtrate is concentrated under vacuum
  6. washwashed with water
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-21fb328397d342f59110714e32a006c2
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

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