Synthesis
1. Add H2O (20 mL) to a 250 mL flask and place in an ice bath to cool. H2SO4 (50 mL) was added slowly to prepare a sulfuric acid solution.
2. To the above sulfuric acid solution, glycerol (12 mL, 16.5 mmol), m-nitrobenzenesulfonic acid sodium salt (11.4 g, 5.06 mmol), and 4-bromo-2-nitroaniline (10 g, 4.6 mmol) were added sequentially.
3. The reaction mixture was heated to 135 °C with continuous stirring for 3 hours.
4. Upon completion of the reaction, the warmed reaction mixture was slowly poured into ice H2O (200 mL).
5. The reaction mixture was extracted with 50% MeOH/EtOAc solvent mixture (2 x 200 mL).
6. The organic phases were combined and dried with Na2SO4, followed by concentration of the organic phase.
7. The resulting brown solid was ground with EtOH and filtered to give the pink solid product 6-bromo-8-nitroquinoline (3.8 g, 33% yield) with a melting point of 172-174 °C.
