Water → 2-[2-(4-Chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione

Participants

Reaction Steps

A mixture of 4-chlorobenzaldehyde tosyl hydrazone sodium salt (1.67 g, 5.05 mmol), benzyltriethylammoniumchloride (115 mg, 0.5 mmol), rhodium acetate (20 mg, 0.05 mmol) and N-vinylphtalimide (4.32 g, 25.0 mmol) in dry 1,4-dioxane (13 ml) was stirred for one day under nitrogen at room temperature. Water (35 ml) was added to the mixture and the aqueous phase was extracted three times with dichloromethane. The combined organic layers were dried over Na2SO4. Evaporation gave the crude material, which was purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 1:1). To afford 392 mg (26.3% of theory) of 2-[2-(4-chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione in the form of a solid.

Provenance & Evidence