Dimethylformamide → 2-bromo-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile

Reaktionsgleichung

[Br:1][C:2]1[CH:9]=[C:8]([CH2:10]Br)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:12]1([C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][O:14]1)=[O:13].[K].C[N:24](C=O)C>>[Br:1][C:2]1[CH:9]=[C:8]([CH2:10][N:24]2[C:12](=[O:13])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

Edukt 3

HCID 6228Dimethylformamide

HCID 534255212-Bromo-4-(bromomethyl)benzonitrile

HCID 67006573Potassium phthalide

Produkt 1

HCID 578135192-bromo-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrileAusbeute 61 %

Versuchsvorschrift

To a solution of 2-bromo-4-(bromomethyl)benzonitrile (18.0 g, 65.5 mmol) in DMF (60 mL), potassium phthalide (18.2 g, 98.2 mmol) was added, and then the mixture was stirred under reflux for 4 h. The reaction was allowed to cool to room temperature. After removing DMF under reduced pressure, the residue was dissolved in CH2Cl2 (200 mL), and washed with water (50 mL×2). The organic layer was dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was recrystallized from toluene and EtOH to give the product, 2-bromo-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile (13.5 g, 61%).