Methanol → 2-[5-Chloro-2-hydroxy benzyl]isoindole-1,3-dione

反応式

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.ClC[C:11]1[CH:19]=[CH:18][CH:17]=[C:13]([C:14](N)=[O:15])[C:12]=1[C:20]([NH2:22])=[O:21].[CH3:23]O>[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:3]=1)[CH2:23][N:22]1[C:20](=[O:21])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:11]=2)[C:14]1=[O:15]

参加物

反応条件

温度: 90 °C

実験手順

To 4-chlorophenol (2.0 g, 15.5 mmol) and chloromethylphthalamide (2.62 g, 13.4 mmol) was added zinc chloride (3 mL, 0.5 M in tetrahydrofuran, 1.5 mmol). The reaction was stirred at 90° C. for 48 hours. After cooling the reaction was diluted with methanol (15 mL) and brought to reflux. After 30 minutes the hot suspension was filtered through a medium glass frit and concentrated to an off-white solid. Methanol (50 mL) was again added and the reaction brought to reflux. After 3 hours the hot suspension was filtered through a medium glass frit and concentrated to an off-white solid. The crude product was purified via chromatography on silica gel to give the title compound (3.86 g).