反応 #49369

反応方程式

potassium iodide

iodine

tert-butyl nitrite

sodium thiosulfate

tert-butyl nitrite

7-Amino-4-phenylisoindolinone

→

7-iodo-4-phenylisoindolinone

収率 61.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度cooling for 1.5 hours
2. 2
   workup.STIRRINGby stirring at 50° C. for 1.5 hours
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄The organic layer was washed with saturated brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   その他The solvent was evaporated under reduced pressure
7. 7
   その他the residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=6/1)

実験手順

7-Amino-4-phenylisoindolinone (80.0 mg, 0.357 mmol) was dissolved in acetonitrile (4.8 mL), and the solution was added with potassium iodide (71.0 mg, 0.428 mmol), copper iodide (82.0 mg, 0.428 mmol), iodine (109 mg, 0.428 mmol) and tert-butyl nitrite (0.068 mL, 0.57 mmol), followed by stirring under ice-cooling for 1.5 hours. Then, the reaction mixture was warmed to room temperature and further added with tert-butyl nitrite (0.068 mL, 0.57 mmol), followed by stirring at 50° C. for 1.5 hours. The reaction mixture was added with 10% aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=6/1) to obtain 7-iodo-4-phenylisoindolinone (72.6 mg, yield 61%).

出典