N-bromobutanimide → 3-bromo-4-methoxyisobenzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

4-methoxyisobenzofuran-1(3H)-one (121) (3.18 g, 19.37 mmol) and 1-bromopyrrolidine-2,5-dione (3.62 g, 20.34 mmol) were dissolved in carbon tetrachloride (40 mL) and heated reflux. (E)-2,2′-(diazene-1,2-diyl)bis(2-methylpropanenitrile) (0.318 g, 1.94 mmol) was added and the reaction stirred overnight at 80° C. The reaction was allowed to cool and filtered. The solvent removed to afford the desired material as a orange solid (3.15 g, 66.9%), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 3.91 (3H, s), 6.66 (1H, s), 7.35-7.40 (2H, m), 7.57-7.65 (1H, m).

Provenance & Evidence