1: 1-(4-fluorophenyl)-1,3-dihydro-5-chloro-isobenzofuran With triphenylphosphine; nickel dichloride; zinc in acetonitrile T=20°C; 0.5 h; 2: potassium cyanide in acetonitrile 8 h; Reflux;

1.1: triphenylphosphine; nickel dichloride; zinc / acetonitrile / 0.5 h / 20 °C 1.2: 8 h / Reflux 2.1: sodium hydride / dimethyl sulfoxide; paraffin oil / 0.17 h / 20 °C / Inert atmosphere 2.2: 0.83 h / 40 °C View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: sulfuric acid / water / 3 h / 160 &deg;C<br />2: thionyl chloride / benzene / 3 h / Reflux<br />3: methanol; sodium tetrahydroborate / <i>tert</i>-butyl alcohol / Reflux<br />4: toluene-4-sulfonic acid / benzene / 2 h / Reflux<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: methanol; sodium tetrahydroborate / <i>tert</i>-butyl alcohol / Reflux<br />2: toluene-4-sulfonic acid / benzene / 2 h / Reflux<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: thionyl chloride / toluene / 20 &deg;C / Reflux<br />2: AlCl₃, aluminium chloride / 0 - 60 &deg;C<br />3: N,N-dimethyl-formamide / 7 h / 110 &deg;C<br />4: sulfuric acid / water / 3 h / 160 &deg;C<br />5: thionyl chloride / benzene / 3 h / Reflux<br />6: methanol; sodium tetrahydroborate / <i>tert</i>-butyl alcohol / Reflux<br />7: toluene-4-sulfonic acid / benzene / 2 h / Reflux<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: AlCl₃, aluminium chloride / 0 - 60 &deg;C<br />2: N,N-dimethyl-formamide / 7 h / 110 &deg;C<br />3: sulfuric acid / water / 3 h / 160 &deg;C<br />4: thionyl chloride / benzene / 3 h / Reflux<br />5: methanol; sodium tetrahydroborate / <i>tert</i>-butyl alcohol / Reflux<br />6: toluene-4-sulfonic acid / benzene / 2 h / Reflux<br /> <br /> &nbsp;