sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-benzyl-N,N,N-triethylammonium chloride in water; benzene 12 h; Ambient temperature;

zinc dibromide in tetrahydrofuran T=-10 - 5°C; 2 h;

zinc dibromide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; diethyl ether -20 deg C to 15 deg C, 30 min 15 deg C; Yield given;

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4123663', constants.ctx, '0')">diisobutylaluminium hydride</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, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-78&deg;C;&nbsp;0.5&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: &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, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=20&deg;C;&nbsp;1.25&nbsp;h;&nbsp;&nbsp;Cooling with iceSealed tubeInert atmosphere;&nbsp;<br />Stage #3: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587194', constants.ctx, '0')">iodine</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, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-10 - 50&deg;C;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;