Reaction #49358

Reaction equation

4-phenoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

TMEDA

sec-butyllithium hexane

iodine

→

4-phenoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

Yield 75.0%

Solvents

THF

Conditions

Workup

1. 1
   Otherfollowed by purification by flash column chromatography (chloroform/methanol=100/0, 99/1)

Procedure

In a similar manner to Step 3 of Example 16, 4-phenoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (700 mg, 1.95 mmol) was dissolved in THF (28 mL), and the solution was treated with TMEDA (0.94 mL, 6.2 mmol), sec-butyllithium-hexane solution (1.01 mol/L, 6.20 mL, 6.24 mmol) and iodine (594 mg, 2.34 mmol), followed by purification by flash column chromatography (chloroform/methanol=100/0, 99/1) to obtain 4-phenoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (708 mg, yield 75%).

Source