Butyl vinyl ether → 1-(6-Fluoroquinolin-8-yl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-fluoro-8-bromo-quinoline (1.53 g, 6.8 mmol) in acetonitrile (35 mL) was added palladium(II) acetate (0.31 g, 1.36 mmol, 0.2 eq.), butyl vinyl ether (2.04 g, 20 mmol, 3.0 eq.), and 1,3-bis(diphenylphosphino)propane (0.70 g, 1.7 mmol, 0.25 eq) was added triethylamine (1.1 g, 11 mmol, 1.6 eq). The resulting mixture was heated to 90° C. for 17 hr and then evaporated under reduced pressure. The residue was dissolved in aqueous hydrochloric acid (2M, 15 mL) and stirred, at room temperature, for 1.5 hr. This mixture was then diluted with water (35 mL) and the pH adjusted with solid sodium hydrogen carbonate until neutral. The mixture was then extracted with ethyl acetate (100 mL); the organic phase was dried over magnesium sulphate. The resulting mixture was filtered and concentrated under reduced pressure to give a brown oil. This crude product was purified by chromatography on silica gel eluting with 10% ethyl acetate in pentane (by volume) to produce the title compound as a pale yellow solid (0.91 g, 71%).

Provenance & Evidence