Toluene → Benzoic Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of the mixture from Example 11 (2.07 g; 8 mmol), triethylamine (6.0 ml; 0.043 mol), and toluene (80 ml) was added diphenylphosphoryl azide (5.0 g; 0.018 mol) and the reaction mixture was heated at 80° C. for 2 hours. The reaction mixture was diluted with acetone (200 ml) and water (40 ml), heated further at 80° C. for 8 hours, cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with 15% ethyl acetate/hexane) to provide benzoic acid, 2-amino-4-bromo, methyl ester (0.514 g) as a white solid and benzoic acid, 2-amino-5-bromo, methyl ester (0.930 g) as a white solid.

Provenance & Evidence