Maleimide → HCID 67508406, compound

Participants

Reaction Steps

To a solution of 4-bromo-2-fluoroaniline (10.0 g, 52.6 mmol) in aqueous HCl (50 mL) was added aqueous NaNO2 (4.0 g, 57.9 mmol) at 0° C. The reaction mixture was stirred for 30 min. To this was added a solution of maleimide (7.65 g, 78.9 mmol) in acetone (50 mL). The pH was adjusted to 3-3.5 by addition of sodium acetate. To the resultant reaction mixture was added CuCl (1.05 g, 7.9 mmol) and it was stirred at 0° C. for 1 h and at r.t. for 6 h. Finally acetone was evaporated and the reaction mixture was diluted with water (20 mL) and extracted with DCM (2×50 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 1:9 EtOAc:Pet. ether) to provide the title compound (2.6 g, 18%) as brown solid.

Provenance & Evidence