Ethyl bromoacetate → ethyl N-phthalimidoxyacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl bromoacetate (2.05 g, 12.3 mmol) in dimethylformamide (15 ml), N-hydroxyphthalimide (3.04 g, 18.4 mmol) and Hunig base (N,N-diisopropylethylamine, 4.24 mL) were added at room temperature, and the mixture was stirred at 80° C. overnight. The reaction solution was poured into saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with ethyl acetate (3×40 ml). The combined organic layer was washed with saturated brine (2×30 ml), dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (100 g, n-hexane/ethyl acetate=2:1) to give (1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-acetic acid ethyl ester (1.83 g, 60%) as a pale yellow solid.

Provenance & Evidence