2-[(E)-4-(1,3-dioxoisoindol-2-yl)but-2-enyl]isoindole-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium phthalimide (20 g, 108 mmol) was added in portions over 2 h to a stirred solution of (E)-1,4-dibromobut-2-ene (10.7 g, 50 mmol ) in DMF (100 ml) at room temperature. The mixture was stirred for a further 3 d at this temperature, then poured into water (100 ml), and the mixture was extracted with dichloromethane (5×100 ml). The organic extracts were dried, filtered and concentrated in vacuo to leave DMF (ca. 30 ml), and a white solid, which was filtered off and washed with ether (3×10 ml) to give (E)-1,4-diphthalimidobut-2-ene (15.75 g, 91%). δH (90 MHz, CDCl3) 4.28 (4H, d), 5.92 (2H, m), and 7.79 (4H, m). the mixture was extracted with dichloromethane (5×100 ml) The organic extracts were dried filtered concentrated in vacuo to leave DMF (ca. 30 ml) a white solid, which was filtered off washed with ether (3×10 ml)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium phathalimide (20 g, 108 mmol) was added in portions over 2 h to a stirred solution of (E)-1,4-dibromobut-2-ene (10.7 g, 50 mmol) in DMF (100 ml) at room temperature. The mixture was stirred for a further 3 days at this temperature, then poured into water (100 ml), and the mixture was extracted with dichloromethane (5×100 ml). The organic extracts were dried, filtered and concentrated in vacuo to leave DMF (ca. 30 ml), and a white solid, which was filtered off and washed with ether (3×10 ml) to give (E)-1,4-diphathalimidobut-2-ene (15.5 g, 91% yield). the mixture was extracted with dichloromethane (5×100 ml) The organic extracts were dried filtered concentrated in vacuo to leave DMF (ca. 30 ml) a white solid, which was filtered off washed with ether (3×10 ml)