Ethyl 5-bromovalerate → 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-pentanoic acid ethyl ester

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This compound was prepared according to the procedure used to prepare 1,3-dihydro-1,3-dioxo-2H-isoindole octanoic acid ethyl ester. Thus, a mixture of 100 g (0.48 mole) of ethyl 5-bromovalerate (99%, Aldrich) and 94.5 g (0.50 mole) of potassium phthalimide (98%, Aldrich) in 300 mL of dimethylformamide gave 107.6 g (81%) of viscous oil. A 2.0 g sample of this oil was purified by high-pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPak® 500 silica; ethyl acetate-hexanes, 1:10). Fractions containing title compound were combined and the solvents evaporated under reduced pressure to give 1.9 g (95% recovery) of colorless liquid.

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