Reaction #49475

Reaction equation

7-amino-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinone

potassium iodide

iodine

tert-butyl nitrate

→

7-iodo-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinone

Yield 62.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherfollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=5/1)

Procedure

In a similar manner to Step 4 of Example 140, 7-amino-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinone (43.0 mg, 0.110 mmol) was dissolved in acetonitrile (6 mL), and the solution was treated with potassium iodide (29.2 mg, 0.176 mmol), copper iodide (33.5 mg, 0.896 mmol), iodine (44.7 mg, 0.896 mmol) and tert-butyl nitrate (0.059 mL, 0.50 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=5/1) to obtain 7-iodo-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinone (33.8 mg, yield 62%).

Source