1.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 2.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 2.2: pH 2 / Inert atmosphere View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: phosphorus tribromide / diethyl ether / 20 &deg;C / Inert atmosphere<br />2: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 &deg;C / Inert atmosphere<br />3: phosphorus tribromide / diethyl ether / 20 &deg;C / Inert atmosphere<br />4: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 &deg;C / Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 &deg;C / Inert atmosphere<br />2: phosphorus tribromide / diethyl ether / 20 &deg;C / Inert atmosphere<br />3: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 &deg;C / Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: Jone's reagent / acetone / 0 - 20 &deg;C<br />2: toluene-4-sulfonic acid / dichloromethane / 36 h / Reflux<br />3: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 &deg;C / Inert atmosphere<br />4: phosphorus tribromide / diethyl ether / 20 &deg;C / Inert atmosphere<br />5: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 &deg;C / Inert atmosphere<br />6: phosphorus tribromide / diethyl ether / 20 &deg;C / Inert atmosphere<br />7: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 &deg;C / Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: toluene-4-sulfonic acid / dichloromethane / 36 h / Reflux<br />2: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 &deg;C / Inert atmosphere<br />3: phosphorus tribromide / diethyl ether / 20 &deg;C / Inert atmosphere<br />4: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 40 h / 20 &deg;C / Inert atmosphere<br />5: phosphorus tribromide / diethyl ether / 20 &deg;C / Inert atmosphere<br />6: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 24 h / 20 &deg;C / Inert atmosphere<br /> <br /> &nbsp;