1: 46 percent / Et3N, PPh3, CCl4 / acetonitrile / 1.) RT, 1 h, 2.) reflux, 3 h 2: 62 percent / 1,2-dichloro-benzene / 8 h / Heating 3: 41 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 4 h / Heating 4: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C 5: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: 83 percent / NBS / CCl₄ / 1 h / Ambient temperature<br />2: 98 percent / Pd(PPh₃)4, aq. Na₂CO₃ / toluene; ethanol / 4 h / 110 &deg;C<br />3: 98 percent / NBS / CCl₄ / 1 h<br />4: 1.) n-BuLi / 1.) Et₂O, hexane, -78 deg C, 1 h, 2.) Et₂O, hexane, RT, 12 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 98 percent / Pd(PPh₃)4, aq. Na₂CO₃ / toluene; ethanol / 4 h / 110 &deg;C<br />2: 98 percent / NBS / CCl₄ / 1 h<br />3: 1.) n-BuLi / 1.) Et₂O, hexane, -78 deg C, 1 h, 2.) Et₂O, hexane, RT, 12 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 98 percent / NBS / CCl₄ / 1 h<br />2: 1.) n-BuLi / 1.) Et₂O, hexane, -78 deg C, 1 h, 2.) Et₂O, hexane, RT, 12 h<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</a> <br />&nbsp;1.) Et₂O, hexane, -78 deg C, 1 h, 2.) Et₂O, hexane, RT, 12 h;&nbsp;&nbsp;Yield given. Multistep reaction;&nbsp;<br /> &nbsp;