Acetone → HCID 85854015, compound

Participants

Reaction Steps

To a stirred solution of 2-chloro-6-hydroxy-quinoline (0.6 g, 3.0 mmol) in acetone (15 ml) potassium carbonate (0.55 g, 4.0 mmol) and 4-fluorobenzylbromide (0.76 g, 4.0 mmol) were added at ambient temperature. Then the reaction mixture was heated to reflux for 3 h. Upon cooling to ambient temperature water was added and the whole mixture extracted twice with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (heptane, ethyl acetate 1:0=>1:4) yielded 2-chloro-6-(4-fluoro-benzyloxy)-quinoline as a white solid (0.19 g, 20%), MS 288.8 [(M+H)+].

Provenance & Evidence