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

반응식

[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

참가 물질

반응물 3

HCID 6228Dimethylformamide

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

HCID 67006573Potassium phthalide

생성물 1

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

실험 절차

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, 4H), 7.36 (s, 1H), 7.23 (s, 1H), 7.15 (s, 1H), 4.77 (s, 2H), 2.30 (s, 3H).