1: 92 percent / Br2 / tetrahydrofuran / 20 °C 2: 96 percent / Br2 / tetrahydrofuran / 20 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: 63 percent / aluminum chloride / CH₂Cl₂ / -20 &deg;C<br />2: 51 percent / ethanol / Heating<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '106417', constants.ctx, '0')">1,3-dimethylpyrazole</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1732991', constants.ctx, '0')">N,N,N',N,-tetramethylethylenediamine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '906717', constants.ctx, '0')">lithium diisopropyl amide</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, '1730733', constants.ctx, '0')">hexane</a> <br />T=-78&deg;C;&nbsp;1&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '606292', constants.ctx, '0')">dimethyl(phenyl)silyl chloride</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, '1730733', constants.ctx, '0')">hexane</a> <br />T=-78 - 20&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: BuLi / tetrahydrofuran; hexane / -78 &deg;C<br />1.2: 97 percent / tetrahydrofuran; hexane / 3 h / 0 &deg;C<br />2.1: 63 percent / aluminum chloride / CH₂Cl₂ / -20 &deg;C<br />3.1: 51 percent / ethanol / Heating<br /> <br /> &nbsp;