Multi-step reaction with 4 steps 1: 90.5 percent / Br2 / Fe / I2 / CCl4 2: 91.6 percent / N-bromsuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating3: 1.)NaOEt / 1.)EtOH, reflux, 2 h, 2.)reflux, 16 h4: 58.7 percent / 5N NaOH / methanol / 2.25 h / Heating  

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '14614139', constants.ctx, '0')">Pd[P(t-Bu)3]2</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=20&deg;C;&nbsp;&nbsp;Schlenk techniqueInert atmosphere;&nbsp;&nbsp;regioselective reaction;&nbsp;<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587159', constants.ctx, '0')">hydrogen iodide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11604118', constants.ctx, '0')">tetrakis(triphenylphosphine) palladium⁽⁰⁾</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635680', constants.ctx, '0')">acetone</a> <br />T=90&deg;C;&nbsp;Carbonylation;&nbsp;reduction;&nbsp;P=68400&nbsp;Torr;&nbsp;42&nbsp;h;&nbsp;<br /> &nbsp;

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3927971', constants.ctx, '0')">n-hexylMgCl</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8128162', constants.ctx, '0')">FeBr₂</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '957171', constants.ctx, '0')">tri-cyclo-hexyl-phosphine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=20&deg;C;&nbsp;0.0833333&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1731256', constants.ctx, '0')">di-isopropyl ether</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=120&deg;C;&nbsp;24&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;&nbsp;Reagent/catalyst;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11536633', constants.ctx, '0')">lithium borohydride</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8128138', constants.ctx, '0')">potassium hydroxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=40&deg;C;&nbsp;3&nbsp;h;&nbsp;&nbsp;Sealed tubeInert atmosphereIrradiation;&nbsp;&nbsp;Overall yield = 37 percent;&nbsp;<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8128138', constants.ctx, '0')">potassium hydroxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=40&deg;C;&nbsp;3&nbsp;h;&nbsp;&nbsp;Sealed tubeInert atmosphereIrradiation;&nbsp;<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8128173', constants.ctx, '0')">palladium dichloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br />T=40&deg;C;&nbsp;24&nbsp;h;&nbsp;&nbsp;Inert atmosphereGreen chemistry;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '16481834', constants.ctx, '0')">Ti(III)-citrate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '19293716', constants.ctx, '0')">Tris buffer</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3571228', constants.ctx, '0')">tetra(n-butyl)ammonium hydroxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11323520', constants.ctx, '0')">B₁₂</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />pH=8;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '14346430', constants.ctx, '0')">&nbsp;Ni(PCy₃)₂Cl₂</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=80&deg;C;&nbsp;0.333333&nbsp;h;&nbsp;<br /> &nbsp;