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

HRID 1032911Notes

Reaction equation

HRID 1032911 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-462a1f5083d043d88c4c09e0bb6216b8
Source dataset
uspto-grants-1994_05
Patent number
US05308837

Reaction notes

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