Glycerol → 5-Bromo-8-fluoroquinoline

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-fluoroaniline (1.0 g, 5.3 mmol) was mixed with glycerol (2.0 mL, 27 mmol), sodium 3-nitrobenzene sulfonate (1.2 g, 5.3 mmol) and concentrated sulfuric acid (8 mL), then the mixture was heated to 140° C. for 2 hours. The inital suspension became a dark brown solution. The mixture was allowed to cool to room temperature. The solution was made basic with 5N NaOH (30 mL), then extracted with EtOAc. The combined organic phase was washed with water then saturated NaCl (aq), dried over MgSO4, filtered, then concentrated to afford the title compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 9.00 (d, J=4.2 Hz, H); 8.54 (d, J=8.6 Hz, 1H); 7.77 (dd, J=8.3, 4.5 Hz, 1H); 7.59 (dd, J=8.6, 4.2 Hz, 1H); 7.32 (dd, J=9.9, 8.3 Hz, 1H). LC4 1.81 min. (M+H)=226.

Provenance & Evidence