Water → 1-(2-amino-5-bromophenyl)-propan-1-one

Participants

Reaction Conditions

Reaction Steps

A three-necked round bottom flask under N2 was charged with AlCl3 (775 mg, 5.81 mmol), then add 5.00 mL of toluene. The slurry was cooled to −10° C. and 4-bromoaniline (1.0 g, 5.81 mmol) was added in one portion. To this was added BCl3 (6.4 mL of 1.0 M solution in xylene) to the mixture at −10° C. slowly, and the mixture was purged with N2 until no more smoke appeared. Propioitrile (1.88 mL, 25.6 mmol) was added and the temperature was allowed to raise to no great than 45° C. The reaction was heated at 63° C. for 10 minutes and maintained at 63° C. for 5 minutes to give a homogeneous solution. Another 4.0 mL of toluene was added into another three-necked flask, and heated to reflux under N2. The solution from previous flask was added to the toluene at reflux over 10 minutes. The mixture was heated to reflux for an additional 4 hours, while continuing to purge the reaction with N2. Toluene would be lost during this process, added more toluene to the mixture if necessary. The reaction was cooled to room temperature and 10 mL of water was added under efficient stirring for ˜30 minutes. The mixture was heated to 55° C. and stirred for 15 minutes before allowing separation into two layers. The organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give a crude solid. The residue was purified though column chromatography (0-50% EtOAc/Heptane gradient) to afford 1-(2-amino-5-bromophenyl)-propan-1-one as a yellow solid (144.0 mg, 10.9%).

Provenance & Evidence