Réaction #73835

Équation de réaction

2-(4-chloro-phenyl)-2-(4-iodo-phenyl)-oxirane

potassium phthalimide

→

title compound

Rendement 34.0%

2-[2-(4-Chloro-phenyl)-2-hydroxy-2-(4-iodo-phenyl)-ethyl]-isoindole-1,3-dione

Rendement 34.0%

Solvants

THF

DMSO

Conditions de réaction

Traitement

1. 1
   ConcentrationThe mixture was concentrated in vacuo
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   Lavagewashed with water and brine (×2)
4. 4
   Séchagedried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   Autreto give a crude product which
8. 8
   Autrewas purified by column chromatography (SiO2)
9. 9
   Lavageeluting with a gradient of ethyl acetate/petrol (2.5% to 100%)

Mode opératoire

A mixture of 2-(4-chloro-phenyl)-2-(4-iodo-phenyl)-oxirane* (571 mg, 1.60 mmol) and potassium phthalimide (340 mg, 1.84 mmol) in THF (5 mL) and DMSO (2 mL) was heated at 100° C. for 20 hours. The mixture was concentrated in vacuo, diluted with ethyl acetate and washed with water and brine (×2), dried (MgSO4), filtered and concentrated to give a crude product which was purified by column chromatography (SiO2), eluting with a gradient of ethyl acetate/petrol (2.5% to 100%) then 10% methanol/dichloromethane to give the title compound (273 mg, 34%); LCMS (PS-A2) Rt 3.22 min [M+H]+ 504.

Source