2-Bromo-4-nitroanisole → 3-Bromo-4-methoxyaniline

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, to a solution of 24.0 g of 2-bromo-1-methoxy-4-nitrobenzene in acetic acid (960 ml) was added 57.0 g of iron then the reaction mixture was warmed to an external temperature of 70° C. over 50 minutes (internal temperature: 63.5° C.). After stirring at the same temperature for 8 hours, the solution was cooled to room temperature. The solid was filtered out, and the filtrate was extracted with CHCl3. The organic layer was washed with a saturated aqueous solution of NaHCO3 and with saturated brine, in this order, then, dried over Na2SO4, and then, the drying agent was removed by filtration and the solvent was evaporated under reduced pressure to obtain 13.1 g of the title compound (brown oil).

Provenance & Evidence