8-Bromo-4-chloro-2-methylquinoline

Uses

8-Bromo-4-chloro-2-methylquinoline is a useful chemical for research.

Synthesis

Part A: To a reaction vial containing 4.76 g (20 mmol) of 8-bromo-2-methylquinolin-4-ol (Ref. J. Org. Chem. 1964, p. 3548) was slowly added 15 mL of phosphoryl chloride under ice bath cooling conditions. The reaction mixture was heated to 100 °C and maintained for 30 min, followed by cooling to room temperature. The unreacted phosphorus trichloride was removed by distillation under reduced pressure. An appropriate amount of ice water was added to the residue, and after adjusting the pH to neutral with ammonia, it was extracted with dichloromethane. The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate as eluent to give 5.0 g of 8-bromo-4-chloro-2-methylquinoline in 97% yield.

References

[1] Patent: US6350750, 2002, B1. Location in patent: Page column 5,6
[2] Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3073 - 3079,7