2-Butene, 1,4-dibromo- → 2-(4-Bromobut-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

HRID 2211308Notes

Reaction equation

HRID 2211308 reaction equation
[Br:1][CH2:2][CH:3]=[CH:4][CH2:5]Br.[K].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12>CN(C=O)C>[Br:1][CH2:2][CH:3]=[CH:4][CH2:5][N:12]1[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]2[C:8]1=[O:18]

Participants

4

Reactant 2

HCID 131802-Butene, 1,4-dibromo-HCID 24194345Phthalimide potassium salt

Product 1

HCID 534234322-(4-Bromobut-2-en-1-yl)-1H-isoindole-1,3(2H)-dioneYield 38.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1,4-dibromo-2-butene (5 g, 23.37 mmol) in 4 mL DMF was added phthalimide potassium salt (433 mg, 2.34 mmol). The reaction mixture was stirred at 40° C. for 16 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated in vacuo to provide the product (250 mg). 1H NMR (CDCl3) δ3.92 (d, 2H); 4.32 (d, 2H); 5.90 (m, 2H); 7.74 (m, 2H); 7.87 (m, 2H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1500d2687a7f430182245ff3d376deed
Source dataset
uspto-grants-1995_10
Patent number
US05463083

Reaction notes

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