1,2-Dibromoethane → 1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethoxy)-

Participants

Reaction Steps

N-(2-Bromoethoxy)phthalimide was synthesised by a modification of the procedure of Bauer and Suresh (Bauer et al 1963). N-Hydroxyphthalimide (80 g, 0.49 mol), triethylamine (150 mL, 1.08 mol), and 1,2-dibromoethane (175 mL, 2.30 mol) were combined in DMF (575 mL) and stirred at room temperature overnight. Solids were filtered and washed with DMF and the filtrate was diluted with water (4.0 L) and the resulting precipitate filtered, dissolved in EtOAc (500 mL), and washed with 1 N HCl (2×100 mL), water (1×100 mL), and dried over MgSO4. Volatiles were removed in vacuo, and the resulting solid recrystallised from 95% EtOH to give (9) as a white solid (87.1 g, 70%): mp. 94-96° C.; lit. mp. 94-96° C. 1H NMR (CDCl3): δ 7.82 (m, 4H), 4.49 (t, 2H, J=6.9 Hz), 3.65 (t, 2H, J=6.9 Hz).

Provenance & Evidence