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

HRID 2229289Notes

Reaction equation

HRID 2229289 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, 2 H); 4.32 (d, 2 H); 5.90 (m, 2 H); 7.74 (m, 2 H); 7.87 (m, 2 H).

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-6a17da11b92b44a6b4c36e52140f7bb2
Source dataset
uspto-grants-2002_07
Patent number
US06420392B1

Reaction notes

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