Réaction #49350

Équation de réaction

TMEDA

sec-butyllithium hexane

iodine

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

→

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

Rendement 40.0%

1-(1-methyl-1-phenylethyl)-3-fluoro-6-iodophtalimide

Rendement 14.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autrefollowed by purification by flash column chromatography (chloroform/methanol=100/0, 85/15)

Mode opératoire

In a similar manner to Step 3 of Example 16, 4-fluoro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (2.06 g, 7.22 mmol) was dissolved in THF (80 mL), and the solution was treated with TMEDA (2.40 mL, 15.9 mmol), sec-butyllithium-hexane solution (0.99 mol/L, 16.0 mL, 15.9 mmol) and iodine (2.20 g, 8.66 mmol), followed by purification by flash column chromatography (chloroform/methanol=100/0, 85/15) to obtain 4-fluoro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (1.19 g, yield 40%) and 1-(1-methyl-1-phenylethyl)-3-fluoro-6-iodophtalimide (425 mg, yield 14%).

Source