Dicyclohexylamine → 1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-4,5,6,7-tetrahydro-

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Reaction Steps

N-(2-Fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide (II: R=isopropyl) (1 g) and dicyclohexylamine (0.01 g) were dissolved in tetrachloroethylene (20 ml), and chlorine (1 ml) was introduced therein at room temperature. The resultant solution was stirred at the room temperature for 2 hours. The reaction mixture was extracted with methylene chloride, and the extract was concentrated. The residue was purified by silica gel chromatography using a mixture of n-hexane and ethyl acetate as an eluent to give 0.9 g of N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide (I: R=isopropyl). M.P., 81°-82° C.

Provenance & Evidence