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

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

Reactant 3

HCID 6228Dimethylformamide

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzene

HCID 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).