Allyl bromide → N-Allylphthalimide

Participants

Reaction Steps

To a mixture of potassium phthalimide (310.39 g, 1.68 mol) in DMF (1.0 L) at 0° C. was added allyl bromide (290.4 mL, 3.36 mol) from a dropping funnel over 30 minutes. The reaction was then warmed to room temperature and allowed to stir for 5 days. The mixture was filtered to remove salts while washing the residue with ethyl acetate (1 L), and the filtrate concentrated under reduced pressure. The residue was then partitioned between saturated aqueous NaHCO3 (0.5 L) and CH2Cl2 (0.8 L) and the organic phase separated. The aqueous phase was extracted with CH2Cl2 (2×0.8 L), and the combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure to give N-allylphthalimide as a white powder (294 g, 94%). 1H NMR (CDCl3) δ 4.30 (d, 2H, J=6.0 Hz), 5.22 (m, 2H), 5.88 (m, 1H), 7.73 (m, 2H), 7.85 (m, 2H).

Provenance & Evidence