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

HRID 2120677Notes

Reaction equation

HRID 2120677 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.[K]>CN(C=O)C.CCOCC>[CH2:2]([N:10]1[C:6](=[O:16])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9]1=[O:11])[CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 2

HCID 21241Homoallyl bromideHCID 24194345Phthalimide potassium salt

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 4-bromo-1-butene (8-3, 20 g, 148 mmol) in DMF (150 mL) was added potassium phthalimide (8-4, 25 g, 133 mmol) and the mixture stirred for 18 hours at 70° C. After cooling to RT, the mixture was diluted with ether, washed with water and brine, dried over MgSO4, and concentrated to give 8-5 as a white solid.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b297bcbe2244dc8ae54dbe23856ff43
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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