Reaction #49363

Reaction equation

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

TMEDA

sec-butyllithium hexane

iodine

→

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

Yield 65.0%

Solvents

THF

Conditions

Workup

1. 1
   Otherfollowed by purification by flash column chromatography (hexane/ethyl acetate=90/10, 70/30)

Procedure

In a similar manner to Step 3 of Example 16, 4-methoxymethoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (8.50 mg, 26.0 mmol) was dissolved in THF (340 mL), and the solution was treated with TMEDA (12.5 mL, 83.1 mmol), sec-butyllithium-hexane solution (0.99 mol/L, 8.4.0 mL, 83.1 mmol) and iodine (7.91 g, 31.2 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=90/10, 70/30) to obtain 4-methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (7.65 g, yield 65%).

Source