Quinoline → 3-Bromo-2-chloro-5-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To phosphorous oxychloride (2.02 ml, 21.6 mmol) was added quinoline (1.34 ml, 11.2 mmol) followed by 3-bromo-2-hydroxy-5-trifluoromethylpyridine (5.0 g, 20.7 mmol), and the mixture formed heated at 120° C. for 3 hrs. It was then cooled to 100° C. and water (10 ml) added. After cooling to 22° C., sodium hydrogen carbonate solution (100 ml) was added and the mixture extracted with ethyl acetate (2×100 ml). The extracts were dried (MgSO4) and concentrated, and the residue purified by silica chromatography to give the product as an oil (4.05 g, 75% yield).

Provenance & Evidence