Ammonia → Benzenamine, 3-bromo-4-methyl-

Participants

Reaction Conditions

Reaction Steps

2-Bromo-4-nitrotoluene (10.0 g, 46.3 mmol) was added to a mixture of water (60 mL), ethanol (130 mL) and acetic acid (40 mL) under nitrogen. The mixture was heated to 70° C. and iron powder (10.3 g, 185 mmol) was added portionwise. After the mixture was heated at refluxed for 2 hours, it was cooled and aqueous ammonia (34%, 180 mL) was added slowly. The mixture is filtered through celite and the aqueous phase was extracted with ethyl acetate. It was dried over MgSO4, filtered, and solvent was removed to give the product as a brown oil (6.0 g, 71%). LCMS (ESI): M+H=185.8.

Provenance & Evidence