Benzaldehyde → N-Benzyl-2,4-difluoroaniline

Participants

Reaction Steps

Magnesium sulfate (5.59 g) and a minor amount of acetic acid were added to a solution of 2,4-difluoroaniline (2.37 ml) and benzaldehyde (2.36 ml) in methanol (46 ml). The mixture was stirred at room temperature for 45 min. Sodium boron hydride (2.64 g) was added thereto under ice cooling, and the mixture was stirred at room temperature for one hr. The solvent was removed by distillation under the reduced pressure. Water and ethyl acetate were added to the residue. The mixture was stirred and was filtered through Celite. The organic layer was extracted with ethyl acetate and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with hexane/acetone (30/1) to give 3.04 g (yield 60%) of the title compound.

Provenance & Evidence