Dimethylformamide → 3-Bromo-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile

HRID 564467Notes

Reaction equation

HRID 564467 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH2:10]Br)[CH:9]=1)[C:5]#[N:6].[C:12]([O-:23])(=O)[C:13]1[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:15]([O-])=[O:16].[K+].[K+].C[N:27](C=O)C>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH2:10][N:27]2[C:15](=[O:16])[C:14]3[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12]2=[O:23])[CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 78125Phthalic acid, dipotassium saltHCID 145678613-Bromo-5-(bromomethyl)benzonitrile

Product 1

HCID 578134473-Bromo-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile

Procedure

A suspension of 3-bromo-5-(bromomethyl)benzonitrile (12.5 g, 45.5 mmol), potassium phthalate (7.16 g, 38.6 mmol), and in DMF (100 mL) was stirred under reflux for 4 h. After cooled to room temperature, the solvent was remove under reduced pressure and the residue was dissolved in CHCl3 (200 mL). The organic layer was washed with water (50 mL×2), dried over Na2SO4, and concentrated in vacuum to obtain 15.2 g of the crude product. The product, 3-bromo-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile (3.50 g, 23%) was purified by flash column chromatography. 1H NMR (400 MHz, CDCl3): δ 7.90-7.87 (m, 2 H), 7.81-7.80 (m, 1 H), 7.77-7.75 (m, 2 H), 7.71-7.70 (m, 1 H), 7.66-7.65 (m, 1 H), 4.83 (s, 2 H).

Workup

  1. temperatureunder reflux for 4 h
  2. customthe solvent was remove under reduced pressure
  3. dissolutionthe residue was dissolved in CHCl3 (200 mL)
  4. washThe organic layer was washed with water (50 mL×2)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-a60bf92873f54784b82db817bd9ff257
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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