1: toluene 2: SOCl2, DMF, Na2CO3 View Scheme

diethyl ether

<b>Multi-step reaction with 3 steps<br /> </b>1: diethyl ether / 1 h / Ambient temperature<br />2: sodium azide, trifluoracetic acid / CHCl₃ / 15 h / 5 - 20 &deg;C<br />3: lithiumaluminium hydride / diethyl ether / 3 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: trichloroacetic acid; benzene; HN₃ <br />2: zinc; aq.-ethanolic HCl<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '506893', constants.ctx, '0')">benzonitrile</a>; <a href="#" onclick="return RXDsubstances(event, this, '606081', constants.ctx, '0')">phenyl-magnesium bromide</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=100&deg;C;&nbsp;Double Grignard addition;&nbsp;0.166667&nbsp;h;&nbsp;&nbsp;Microwave irradiation;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '3535220', constants.ctx, '0')">methylmagnesium bromide</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '10775048', constants.ctx, '0')">titanium(IV) isopropylate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a> <br />T=50&deg;C;&nbsp;Double Grignard addition;&nbsp;1&nbsp;h;&nbsp;&nbsp;Microwave irradiation;&nbsp;<br /> &nbsp;