3-Bromocyclohexene → 2-(Cyclohex-2-enyl)isoindoline-1,3-dione

HRID 2280722Notes

Reaction equation

HRID 2280722 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.[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.[K]>CN(C=O)C.O>[CH:2]1([N:12]2[C:8](=[O:18])[C:9]3[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:11]2=[O:13])[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 1370573-BromocyclohexeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 105854002-(Cyclohex-2-enyl)isoindoline-1,3-dioneYield 73,717.898%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-cyclohexene (500 g, 3.12 mmol) in DMF (2000 mL) was added potassium phtalimide (580 g, 3.12 mmol), and the reaction mixture was stirred at room temperature for 30 h. The reaction mixture was diluted with water (1000 mL), extracted with ethyl acetate (3 times), and the combined organic layers were concentrated to give 2-cyclohex-2-enyl-isoindole-1,3-dione (520 g, 2.30 mol) as a gray solid.

Workup

  1. extractionextracted with ethyl acetate (3 times)
  2. concentrationthe combined organic layers were concentrated

Sources & evidence

ORD record
ord-61ac3e42ca894ea0899d22e14b4a0e2e
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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