Benzyl Bromide → Dibenzyl-(2,4-difluoro-phenyl)-amine

Participants

Reaction Steps

To 2,4-difluoroaniline (40.0 g, 0.31 mol) in N,N-dimethylformamide (400 mL) were added potassium carbonate (120 g, 0.92 mol, 3 eq) and benzyl bromide (112 mL, 0.71 mmol, 2.3 eq). The reaction was stirred with mechanical stirring at room temperature overnight. In order to quench the benzyl bromide in excess, NH4OH (90 mL) was added and the reaction was stirred overnight. The mixture was filtered and DMF was evaporated under reduced pressure. Ethyl acetate was added and the organic layer was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the oily crude was crystallized in methanol, obtaining after drying 71 g of dibenzyl-(2,4-difluoro-phenyl)-amine as a white solid (74%)

Provenance & Evidence