palladium 10 on activated carbon; hydrogen in methanol T=60°C; P=760.051 Torr; 8 h;

boron tribromide in dichloromethane T=-60°C; 12 h;

lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium(0); [(t-Bu)3PH]BF4

1: bromine; pyridine / tetrachloromethane / 3 h / 0 - 90 °C 2: potassium carbonate; water / methanol / 2 h / 20 °C 3: potassium carbonate / acetone / 20 °C 4: potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / |Inert atmosphere 5: palladium 10 on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr View Scheme

1: potassium carbonate; water / methanol / 2 h / 20 °C 2: potassium carbonate / acetone / 20 °C 3: potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / |Inert atmosphere 4: palladium 10 on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr View Scheme

1: potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / |Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr View Scheme

1: pyridine / dichloromethane / 8 h / 0 - 20 °C 2: bromine; pyridine / tetrachloromethane / 3 h / 0 - 90 °C 3: potassium carbonate; water / methanol / 2 h / 20 °C 4: potassium carbonate / acetone / 20 °C 5: potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / |Inert atmosphere 6: palladium 10 on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr View Scheme

1.1: hydrogenchloride / water / 0.17 h 1.2: 0.33 h / |Inert atmosphere; |Reflux 1.3: 50 h / |Reflux; |Inert atmosphere 2.1: hydrogenchloride; tin (II) chloride dihydrate / 0.22 h / 50 °C 3.1: boron tribromide / dichloromethane / 12 h / -60 °C View Scheme

1: hydrogenchloride; tin (II) chloride dihydrate / 0.22 h / 50 °C 2: boron tribromide / dichloromethane / 12 h / -60 °C View Scheme

1: iron; hydrogenchloride / ethanol; water / 2 h / |Reflux 2: phosphoric acid / water / 72 h / 180 °C / |Autoclave 3: [(t-Bu)3PH]BF4; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium(0) View Scheme