1: 87 percent / K2CO3 / dimethylformamide / 24 h / 60 °C 2: 1.) BuLi, CuBr*SMe2, 2.) Me3SiCl / 1.) Et2O, hexane, THF, -78 deg C, 1 h, 2.) THF, Et2O, hexane, -78 deg C, 1.5 h View Scheme

1: 51 percent / aq. NaOH / 3 h / 0 - 20 °C 2: 70 percent / Br2, AcOH / 48 h / Ambient temperature 3: 87 percent / K2CO3 / dimethylformamide / 24 h / 60 °C 4: 1.) BuLi, CuBr*SMe2, 2.) Me3SiCl / 1.) Et2O, hexane, THF, -78 deg C, 1 h, 2.) THF, Et2O, hexane, -78 deg C, 1.5 h View Scheme

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 20 °C 1.2: 41 percent / tetrahydrofuran / 6 h / Heating 2.1: 78 percent / sodium amalgam; sodium phosphate / methanol / 2 h / 20 °C View Scheme

1: sodium nitrite; NH4BF4 / ethanol / 0.5 h / 0 °C / |Inert atmosphere 2: sodium acetate; palladium diacetate / methanol / 16 h / 20 °C / |Inert atmosphere 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / 16 h / 0 - 20 °C / |Inert atmosphere 4: palladium 10 on activated carbon; hydrogen / #tert!-butyl alcohol; water / 5 h / 60 °C / 7500.75 Torr / |Autoclave; |Inert atmosphere View Scheme

1: sodium hydrogencarbonate / methanol / 2 h / 20 °C / |Inert atmosphere 2: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C / |Inert atmosphere 3: water; hydrogenchloride / ethanol / 5 h / 80 °C / |Inert atmosphere 4: sodium nitrite; NH4BF4 / ethanol / 0.5 h / 0 °C / |Inert atmosphere 5: sodium acetate; palladium diacetate / methanol / 16 h / 20 °C / |Inert atmosphere 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / 16 h / 0 - 20 °C / |Inert atmosphere 7: palladium 10 on activated carbon; hydrogen / #tert!-butyl alcohol; water / 5 h / 60 °C / 7500.75 Torr / |Autoclave; |Inert atmosphere View Scheme

1: 24 h / 20 °C / |Inert atmosphere 2: sodium hydrogencarbonate / methanol / 2 h / 20 °C / |Inert atmosphere 3: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C / |Inert atmosphere 4: water; hydrogenchloride / ethanol / 5 h / 80 °C / |Inert atmosphere 5: sodium nitrite; NH4BF4 / ethanol / 0.5 h / 0 °C / |Inert atmosphere 6: sodium acetate; palladium diacetate / methanol / 16 h / 20 °C / |Inert atmosphere 7: 1,8-diazabicyclo[5.4.0]undec-7-ene / 16 h / 0 - 20 °C / |Inert atmosphere 8: palladium 10 on activated carbon; hydrogen / #tert!-butyl alcohol; water / 5 h / 60 °C / 7500.75 Torr / |Autoclave; |Inert atmosphere View Scheme

1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C / |Inert atmosphere 2: water; hydrogenchloride / ethanol / 5 h / 80 °C / |Inert atmosphere 3: sodium nitrite; NH4BF4 / ethanol / 0.5 h / 0 °C / |Inert atmosphere 4: sodium acetate; palladium diacetate / methanol / 16 h / 20 °C / |Inert atmosphere 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / 16 h / 0 - 20 °C / |Inert atmosphere 6: palladium 10 on activated carbon; hydrogen / #tert!-butyl alcohol; water / 5 h / 60 °C / 7500.75 Torr / |Autoclave; |Inert atmosphere View Scheme

1: water; hydrogenchloride / ethanol / 5 h / 80 °C / |Inert atmosphere 2: sodium nitrite; NH4BF4 / ethanol / 0.5 h / 0 °C / |Inert atmosphere 3: sodium acetate; palladium diacetate / methanol / 16 h / 20 °C / |Inert atmosphere 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / 16 h / 0 - 20 °C / |Inert atmosphere 5: palladium 10 on activated carbon; hydrogen / #tert!-butyl alcohol; water / 5 h / 60 °C / 7500.75 Torr / |Autoclave; |Inert atmosphere View Scheme

n-butyllithium; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex 1.) Et2O, hexane, THF, -78 deg C, 1 h, 2.) THF, Et2O, hexane, -78 deg C, 1.5 h; Yield given. Multistep reaction;

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