Dimethylformamide → 2-[(3-bromo-5-methylphenyl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 564446Notes

Reaction equation

HRID 564446 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9]Br)[CH:3]=1.[C:11]1([C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][O:13]1)=[O:12].[K].C[N:23](C=O)C>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][N:23]2[C:11](=[O:12])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:13])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzeneHCID 67006573Potassium phthalide

Product 1

HCID 578134412-[(3-bromo-5-methylphenyl)methyl]-1H-isoindole-1,3(2H)-dioneYield 67%

Procedure

To a solution of 1-bromo-3-(bromomethyl)-5-methylbenzene (34.0 g, 128.8 mmol) in DMF (200 mL), was added potassium phthalide (28.9 g, 154.6 mmol), and the mixture was stirred under reflux for 2 h. The reaction was allowed to cool to room temperature. After the solvent was remove under reduced pressure, the residue was dissolved in CH2Cl2 (300 mL), and washed with water (50 mL×3). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent gave a white solid. The solid was recrystallized from toluene and EtOH to give the product, 2-[(3-bromo-5-methylphenyl)methyl]-1H-isoindole-1,3(2H)-dione (28.5 g, 67%). 1H NMR (400 MHz, CDCl3): δ 7.87-7.72 (m, 4 H), 7.36 (s, 1H), 7.23 (s, 1 H), 7.15 (s, 1 H), 4.77 (s, 2 H), 2.30 (s, 3 H).

Workup

  1. temperatureunder reflux for 2 h
  2. customAfter the solvent was remove under reduced pressure
  3. dissolutionthe residue was dissolved in CH2Cl2 (300 mL)
  4. washwashed with water (50 mL×3)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customEvaporation of the solvent
  7. customgave a white solid
  8. customThe solid was recrystallized from toluene and EtOH

Sources & evidence

ORD record
ord-d3361df022ff41b998f0dc64a9effee9
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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