Water → 4-Bromo-2-nitrobenzoic acid

Participants

Reaction Steps

A mixture of 4-bromo-2-nitrotoluene (5.0 g, 23 mmol), KMnO4 (10.9 g, 69 mmol), and water (250 mL) was heated at reflux overnight. The mixture was filtered through a pad of diatomaceous earth, washing with water. The basic filtrate was acidified to pH˜1 with conc. HCl and extracted with EtOAc (3×300 mL). The combined organic layers were dried (MgSO4) and concentrated to provide the desired benzoic acid (1.22 g, 22%). MS (ESI−): mass calcd. for C7H4BrNO4, 244.9; m/z found, 244 [M−H]−. 1H NMR (400 MHz, CD3OD): 8.07 (d, J=1.9, 1H), 7.85 (dd, J=8.2, 1.9, 1H), 7.65 (d, J=8.2, 1H).

Provenance & Evidence