trans-1,4-Dibromo-2-butene → 2-(4-Bromobut-2-en-1-yl)isoindoline-1,3-dione

HRID 36581

Reaction equation

HRID 36581 reaction equation
[Br:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5]Br.[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.[K]>CN(C)C=O>[Br:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][N:11]1[C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]2[C:7]1=[O:17]

Participants

4

Reactant 2

HCID 641245trans-1,4-Dibromo-2-buteneHCID 24194345Phthalimide potassium salt

Product 1

HCID 105168412-(4-Bromobut-2-en-1-yl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of trans-1,4-dibromo-2-butene (6.4 g, 30 mmol) and potassium phthalimide (5.6 g, 30 mmol) in anhydrous dimethyl formamide (200 ml) was heated at 50° C. for 24 h. Then the reaction mixture was concentrated in vacuo, dissolved in ethyl acetate, washed with brine and the pure title product was obtained by flash chromatography on silica gel (ethyl acetate: hexane; 15:85) (3.2 g, 40%).

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with brine

Sources & evidence

ORD record
ord-ee15fbcd76dc40cc8c92ef9b7b59c2d5
Source dataset
uspto-grants-1995_05
Patent number
US05416076

Linked notes

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