1.1: iodine / tetrahydrofuran; toluene / 20 h / Irradiation 2.1: 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl acetamide / 20 °C / Inert atmosphere 2.2: 100 - 140 °C / Inert atmosphere View Scheme

1.1: iodine / tetrahydrofuran; toluene / 20 h / Irradiation 2.1: 1,3-bis-(diphenylphosphino)propane; palladium diacetate / N,N-dimethyl acetamide / 20 °C / Inert atmosphere 2.2: 100 - 140 °C / Inert atmosphere View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 3 h / 150 &deg;C / Heating<br />2.1: NaH / dimethylformamide; various solvent(s) / 0.33 h / cooling<br />2.2: 81 percent / dimethylformamide<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '606498', constants.ctx, '0')">4-bromo-benzyl bromide</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '956578', constants.ctx, '0')">triethyl phosphite</a> <br />T=160&deg;C;&nbsp;0.5&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4122952', constants.ctx, '0')">sodium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=0&deg;C;&nbsp;1&nbsp;h;&nbsp;<br />Stage #3: <a href="#" onclick="return RXDsubstances(event, this, '507750', constants.ctx, '0')">β-naphthaldehyde</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />4&nbsp;h;&nbsp;<br /> &nbsp;