carbon tetrabromide; triphenylphosphine in dichloromethane T=0 - 20°C;

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1361988', constants.ctx, '0')">oxalyl dichloride</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=0 - 20&deg;C;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4212332', constants.ctx, '0')">tetra-N-butylammonium borohydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-78&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: i-Pr₂NEt / tetrahydrofuran / 0 &deg;C<br />2.1: hydrogen / Pd(OH)2 on carbon / ethanol / 760 Torr<br />3.1: oxalyl chloride; DMF / CH₂Cl₂ / 0 - 20 &deg;C<br />3.2: Bu₄NBH₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: Rh₂(OAc)4 / tetrahydrofuran; H₂O / Heating<br />2.1: i-Pr₂NEt / tetrahydrofuran / 0 &deg;C<br />3.1: hydrogen / Pd(OH)2 on carbon / ethanol / 760 Torr<br />4.1: oxalyl chloride; DMF / CH₂Cl₂ / 0 - 20 &deg;C<br />4.2: Bu₄NBH₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: hydrogen / Pd(OH)2 on carbon / ethanol / 760 Torr<br />2.1: oxalyl chloride; DMF / CH₂Cl₂ / 0 - 20 &deg;C<br />2.2: Bu₄NBH₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: DMAP / toluene / Heating<br />2.1: p-toluenesulfonylazide; Et₃N / acetonitrile / 0 - 20 &deg;C<br />3.1: Rh₂(OAc)4 / tetrahydrofuran; H₂O / Heating<br />4.1: i-Pr₂NEt / tetrahydrofuran / 0 &deg;C<br />5.1: hydrogen / Pd(OH)2 on carbon / ethanol / 760 Torr<br />6.1: oxalyl chloride; DMF / CH₂Cl₂ / 0 - 20 &deg;C<br />6.2: Bu₄NBH₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1.1: MgCl₂; Et₃N / acetonitrile<br />2.1: DMAP / toluene / Heating<br />3.1: p-toluenesulfonylazide; Et₃N / acetonitrile / 0 - 20 &deg;C<br />4.1: Rh₂(OAc)4 / tetrahydrofuran; H₂O / Heating<br />5.1: i-Pr₂NEt / tetrahydrofuran / 0 &deg;C<br />6.1: hydrogen / Pd(OH)2 on carbon / ethanol / 760 Torr<br />7.1: oxalyl chloride; DMF / CH₂Cl₂ / 0 - 20 &deg;C<br />7.2: Bu₄NBH₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;