1.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -80 - -35 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 24 h / 35 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 0 - 20 °C 4.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / 1 h / -15 °C 4.2: -15 - 12 °C View Scheme

1: With hydrogen; palladium on activated carbon in methanol T=50°C; P=2250.23 Torr; Inert atmosphere; 2: With 1,3-dibromo-5,5-dimethyl-hydantoin in methanol T=40°C;

1,1,3,3-tetramethyldisiloxane; trifluoroacetic acid in 1,2-dichloro-ethane T=-20 - -10°C; 0.25 h; Inert atmosphere;

hydrogen bromide; hydrogen; 5 palladium on charcoal in methanol; water T=20°C; P=3102.97 Torr; 0.25 h; Inert atmosphere; Product distribution / selectivity;

1: tetrahydrofuran / 1 h / -15 - 0 °C 2: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr 3: N-bromosuccinmide / acetonitrile / 35 °C View Scheme

1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / ethanol; water / 1 h / 40 °C / 775.74 Torr 2: N-bromosuccinmide / acetonitrile / 35 °C View Scheme

1.1: tetrahydrofuran / 3.5 h / -10 - 4 °C / Inert atmosphere; Large scale reaction 1.2: -10 - 20 °C / Large scale reaction 2.1: 1,1,3,3-tetramethyldisiloxane; trifluoroacetic acid / 1,2-dichloro-ethane / -20 - -5 °C / Inert atmosphere; Large scale reaction View Scheme

1.1: tetrahydrofuran / 4 h / 65 °C 2.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 1.17 h / 0 - 10 °C / Inert atmosphere; Large scale reaction 2.2: 0 - 20 °C / Large scale reaction 3.1: tetrahydrofuran / 3.5 h / -10 - 4 °C / Inert atmosphere; Large scale reaction 3.2: -10 - 20 °C / Large scale reaction 4.1: 1,1,3,3-tetramethyldisiloxane; trifluoroacetic acid / 1,2-dichloro-ethane / -20 - -5 °C / Inert atmosphere; Large scale reaction 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 View Scheme

n-butyllithium in tetrahydrofuran; hexane; toluene T=-80 - -35°C; 0.5 h; Inert atmosphere;