Sodium Acetate → 2,6-Dibromo-4-methylbenzaldehyde (2,4-difluorophenyl)hydrazone

Participants

Reaction Steps

2,6-Dibromo-4-methylbenzaldehyde (89.5 g, 0.322 mol), (2,4-difluorophenyl)hydrazine hydrochloride (58.25 g, 0.322 mol) and sodium acetate (26.9 g, 0.328 mol) were heated in methanol (1.25 L) at reflux for 3.5 hours. The mixture was cooled and the precipitate was collected by filtration and partitioned between ethyl acetate (750 mL) and water (250 mL). The ethyl acetate layer was combined with a second ethyl acetate extract, washed successively with water and brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to afford the title compound as an off-white solid (97.5 g).

Provenance & Evidence