Allyl bromide → N-Allyloxyphthalimide

Participants

Reaction Steps

To a cooled solution (5 to 10° C.) of N-hydroxyphthalimide (53.80 g, 0.33 mol) in DMF (120 mL), was added DBU (46.36 mL, 0.31 mol) was added in one portion, with stirring. After 10 minutes, allyl bromide (25.96 mL, 0.30 mol) was added in portions. The cooling bath was removed and the reaction mixture was stirred at room temperature for 1 hour, until the color turned from dark burgundy to yellow. Ethyl acetate (300 mL) and water (150 mL) were added, the aqueous phase was separated, and the organic phase was washed with water (4×50 mL). The combined aqueous extracts were back-extracted with EtOAc (3×50 mL) and the total EtOAc solution was washed with saturated NaHCO3 (10×50 mL) until the aqueous phase was pale yellow, then with brine (2×75 mL) and dried over anhydrous MgSO4. Removal of the solvent afforded 58.83 g (96% yield) of the product as a white solid.

Provenance & Evidence