반응 #49369

반응 방정식

potassium iodide

iodine

tert-butyl nitrite

sodium thiosulfate

tert-butyl nitrite

7-Amino-4-phenylisoindolinone

→

7-iodo-4-phenylisoindolinone

수율 61.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도cooling for 1.5 hours
2. 2
   workup.STIRRINGby stirring at 50° C. for 1.5 hours
3. 3
   추출extracted with ethyl acetate
4. 4
   세척The organic layer was washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The solvent was evaporated under reduced pressure
7. 7
   기타the residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=6/1)

실험 절차

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%).

출처