Dimethylformamide → N-3-Bromopropylphthalimide

Participants

Reaction Conditions

Reaction Steps

To a solution of dibromopropane (0.61 mL, 6.0 mmol) in DMF (8 mL) was added potassium phthalimide (0.2756 g, 1.5 mmol), and was stirred at 90° C. for 17 hours. The mixture was concentrated, 1N NaOH (10 mL) was added, and extracted with CH2Cl2 (2×30 mL). The combined organic extracts were washed with water (1×15 mL), dried (Na2SO4), and concentrated. Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc) provided 0.1977 g (49%) of 2-(3-bromo-propyl)-isoindole-1,3-dione as a white solid. 1H NMR (CDCl3) δ 2.21-2.30 (m, 2H), 3.41 (t, 2H, J=6.0 Hz), 3.83 (t, 2H, J=6.0 Hz), 7.69-7.75 (m, 2H), 7.82-7.86 (m, 2H).

Provenance & Evidence