Yield given. Multistep reaction;

1.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1 h / -10 - 5 °C 2.1: tetrahydrofuran / 1 h / -15 - 0 °C 3.1: trifluoroacetic acid; 1,1,3,3-tetramethyldisiloxane / 1,2-dichloro-ethane / 0.25 h / -20 - -10 °C 4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 4.2: 1 h / 15 - 20 °C / pH 2 5.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 32 h / 20 - 45 °C / Inert atmosphere 6.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 10 - 20 °C 7.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 7.2: -10 - 12 °C View Scheme

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 °C / |Inert atmosphere 1.2: 0.83 h / -78 °C / |Inert atmosphere 2.1: potassium carbonate / ethylene glycol dimethyl ether / 4 h / 20 °C / |Inert atmosphere 2.2: 16 h / 100 °C / |Inert atmosphere View Scheme

n-butyllithium in tetrahydrofuran

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.0833333 h; Inert atmosphere; 2: With boric acid trimethyl ester in tetrahydrofuran; diethyl ether; hexane T=-50°C; 0.5 h; Inert atmosphere; 3: With hydrogenchloride in tetrahydrofuran; diethyl ether; hexane; water T=20°C;

in 1-methyl-pyrrolidin-2-one T=180°C; 5.5 h;

tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=100°C; 10 h; Inert atmosphere;

1.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1 h / -10 - 5 °C 2.1: tetrahydrofuran / 1 h / -15 - 0 °C 3.1: trifluoroacetic acid; 1,1,3,3-tetramethyldisiloxane / 1,2-dichloro-ethane / 0.25 h / -20 - -10 °C 4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 4.2: 1 h / 15 - 20 °C / pH 2 View Scheme

1.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1.17 h / 0 - 10 °C / Inert atmosphere; Large scale reaction 1.2: 0 - 20 °C / Large scale reaction 2.1: tetrahydrofuran / 3.5 h / -10 - 4 °C / Inert atmosphere; Large scale reaction 2.2: -10 - 20 °C / Large scale reaction 3.1: 1,1,3,3-tetramethyldisiloxane; trifluoroacetic acid / 1,2-dichloro-ethane / -20 - -5 °C / Inert atmosphere; Large scale reaction 4.1: potassium phosphate; [Ru(II)(η6-benzene)(μ-Cl)Cl]2; potassium acetate; triphenylphosphine / 1-methyl-pyrrolidin-2-one / 9 h / 110 - 130 °C / Inert atmosphere; Large scale reaction 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.75 h / 20 - 62 °C / Inert atmosphere; Large scale reaction 6.1: sodium tetrahydroborate / tetrahydrofuran; water / 17.92 h / 0 - 22 °C / Inert atmosphere; Large scale reaction 6.2: 0 - 20 °C / Inert atmosphere; Large scale reaction View Scheme

AlCl3, aluminium chloride in 1,2-dichloro-ethane T=-10 - 5°C; 1 h;