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

HRID 657320Notes

Reaction equation

HRID 657320 reaction equation
[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]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 534255212-Bromo-4-(bromomethyl)benzonitrileHCID 67006573Potassium phthalide

Product 1

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

Procedure

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%).

Workup

  1. temperatureunder reflux for 4 h
  2. customAfter removing DMF under reduced pressure
  3. dissolutionthe residue was dissolved in CH2Cl2 (200 mL)
  4. washwashed with water (50 mL×2)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was recrystallized from toluene and EtOH

Sources & evidence

ORD record
ord-9b0af153a1b444c0b14e31bbc1e3bc42
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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