selenium T=350°C;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11378922', constants.ctx, '0')">palladium on activated charcoal</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />&nbsp;Hydrogenation;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: Mg / diethyl ether / Heating<br />1.2: diethyl ether / 20 &deg;C<br />2.1: aq. HCl / CH₂Cl₂ / 0.5 h<br />3.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />4.1: 71 percent / Na / ethanol / 1.25 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>2: 96 percent / borane-dimethyl sulphide / diethyl ether / 1 h / Heating<br />3: Et₃N / diethyl ether / 3 h / Ambient temperature<br />4: LiBr / acetone / 6 h / Heating<br />5: 80 percent / benzene / 20 h / Heating<br />6: 1) n-BuLi / 1) THF, -25 degC, 15 min.; 2) THF, room temp., 2 h.<br />7: 42 percent / BF₃-etherate / CH₂Cl₂ / 15 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: Mg / diethyl ether / Heating<br />1.2: diethyl ether / 20 &deg;C<br />2.1: aq. HCl / CH₂Cl₂ / 0.5 h<br />3.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 0.25 h / 20 &deg;C<br />4.1: 71 percent / Na / ethanol / 1.25 h / Heating<br /> <br /> &nbsp;