5-bromo-4-chloro-2-methylaniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 5-bromo-4-chloro-2-methylaniline (1 g, 4.54 mmol) in acetic acid (10 mL) was added a solution of sodium nitrite (0.329 g, 4.76 mmol) in water (1 mL). The mixture was heated at reflux for 2 hours and was subsequently cooled and concentrated. The residue was partitioned in water and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to give the title compound as a red-brown solid (0.67 g, 64%). ESI-MS m/z [M+H]+ 232.2. The mixture was heated at reflux for 2 hours was subsequently cooled concentrated The residue was partitioned in water extracted with EtOAc The combined organic layers were washed with brine dried over magnesium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 5-bromo-4-chloro-2-methylaniline (1 g, 4.54 mmol) in acetic acid (10 mL) was added a solution of sodium nitrite (0.329 g, 4.76 mmol) in water (1 mL). The mixture was heated at reflux for 2 hours and was subsequently cooled and concentrated. The residue was partitioned in water and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to give the title compound as a red-brown solid (0.67 g, 64%). ESI-MS m/z [M+H]+ 232.2. The mixture was heated at reflux for 2 hours was subsequently cooled concentrated The residue was partitioned in water extracted with EtOAc The combined organic layers were washed with brine dried over magnesium sulfate concentrated