Water → N-(12-Bromododecyl)phthalimide

Participants

Reaction Conditions

Reaction Steps

1,12-dibromododecane (32.22 g, 98.2 mmol), potassium phthalimide (4.60 g, 24.5 mmol), and dimethylformamide (20 mL) were combined and refluxed at 160° C. for 2.5 hours. Upon cooling, water was added and the organic taken into dichloromethane (separated on a separatory funnel). The solvent was evaporated under reduced pressure and the crude product was columned in hexanes. The spots were not separated, and the fractions were combined, the solvent removed, and the crude material re-dissolved in 300 mL acetone. This was refluxed, and 10 g potassium phthalimide was added over 4 hours. The mixture was refluxed overnight. After cooling and removing the solvent, the crude product was columned using 1:1 ethyl acetate: hexanes. The top spot proved to be the desired product, which was collected as a white solid (9.30 g) that matched the reported literature: Helv. Chimica Acta. 2001, 84(3), 678-689.

Provenance & Evidence