Ethyl 3-bromopropionate → Ethyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate

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Reaction Steps

This compound was prepared according to the procedure used to prepare 1,3-dihydro-1,3-dioxo-2H-isoindoleoctanoic acid ethyl ester. Thus, a mixture of 100.0 g (0.55 mole) of 3-bromopropionic acid ethyl ester (99%, Aldrich) and 108.7 g (0.58 mole) of potassium phthalimide (98%, Aldrich) in 300 mL of dimethylformamide gave 59.4 g (44%) of crude title compound as an oily residue. A 3.0 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 2.3 g (77% recovery) of a pale-yellow oil.

Provenance & Evidence