1.1: hydrogen / 5 palladium on charcoal / methanol / 20 °C / 1551.49 Torr / Inert atmosphere 2.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 10 - 20 °C 3.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 3.2: -10 - 12 °C View Scheme

hydrogen; 5 palladium on charcoal in methanol T=20°C; P=1551.49 Torr; Inert atmosphere;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: N-bromosuccinmide / acetonitrile / 60 &deg;C<br />2.1: sulfuric acid / 12 h / Reflux<br />3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 &deg;C / Inert atmosphere<br />3.2: -35 &deg;C<br />4.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 &deg;C / Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: tetrahydrofuran / 5 h / 65 - 68 &deg;C<br />2.1: AlCl₃, aluminium chloride / 1,2-dichloro-ethane / 1 h / -10 - 5 &deg;C<br />3.1: tetrahydrofuran / 1 h / -15 - 0 &deg;C<br />4.1: sulfuric acid / 12 h / Reflux<br />5.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 &deg;C / Inert atmosphere<br />5.2: -35 &deg;C<br />6.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 &deg;C / Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: tetrahydrofuran / 1 h / -15 - 0 &deg;C<br />2.1: N-bromosuccinmide / acetonitrile / 60 &deg;C<br />3.1: sulfuric acid / 12 h / Reflux<br />4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 &deg;C / Inert atmosphere<br />4.2: -35 &deg;C<br />5.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 &deg;C / Inert atmosphere<br /> <br /> &nbsp;