Ethyl Acetate → 2,5-Dibromo-3,6-difluoroaniline

Participants

Reaction Conditions

Reaction Steps

2,5-Dibromo-3,6-difluoronitrobenzene (120 g, 0.37 mol) is dissolved in a mixture of ethanol (300 mL) and concentrated HCl (500 mL). The mixture is heated to 80° C. and treated with iron powder (100 g, 1.78 mol) by portion-wise addition over 2 hours. After stirring for an additional hour, the mixture is cooled to room temperature and EtOAc (800 mL) is added. The solids are removed by filtration and then the solution concentrated by rotary evaporator to remove most of the solvent. The residue is partitioned between EtOAc (1000 mL) and water (500 mL). The organic layer is washed with brine (2×250 mL), dried (MgSO4) and concentrated by rotary evaporator to give a brown oil. The crude product is then purified using flash chromatography (9:1 hexanes/EtOAc) to give 2,5-dibromo-3,6-difluoroaniline.

Provenance & Evidence