hydrogen bromide; iron tribromide in dichloromethane T=25°C; 0.2 h;

1: 1.) solid KOH 2.) 1N HCl / benzyltriethylammonium chloride / 1.) CH2Cl2, 20 deg C. Var.: 50 percent aq. NaOH instead of KOH 2: aq. NaOH View Scheme

hydrogenchloride; lithium hydroxide; potassium carbonate; tetrabutylammomium bromide 1.) acetonitrile, reflux, 1 h, 2.) methanol, 1 h, 3.) 20 deg C; Yield given. Multistep reaction;

1.1: n-BuLi / tetrahydrofuran / 0.75 h / -78 °C 1.2: tetrahydrofuran / -78 - 20 °C 1.3: aq. HCl / 1 h / Heating 2.1: BH3*SMe2 / tetrahydrofuran / 0 - 20 °C View Scheme

(i) Mg, (ii) /BRN= 102378/; Multistep reaction;

sodium hydride 1.) DMF, 2.) DMF, room temp., 15 h;

in water; N,N-dimethyl-formamide

1.1: magnesium; iodine / diethyl ether / 0.25 h / Heating 1.2: 57 percent / diethyl ether / 2 h / Heating 2.1: sodium hydride / dimethylformamide / 4.5 h / 70 - 80 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 4 h / -15 °C / |Inert atmosphere; |Large scale 2.1: N,N-dimethyl-formamide / toluene / 1.5 h / |Inert atmosphere; |Large scale 3.1: potassium carbonate; O,N-dimethyl-hydroxylamine hydrochloride / water / 1.25 h / 30 °C / |Inert atmosphere; |Large scale 3.2: 1.5 h / |Inert atmosphere; |Large scale 4.1: potassium tert-butylate; C62H66Cl2N2P2Ru / toluene; isopropyl alcohol / 0 - 25 °C / |Inert atmosphere; |Glovebox; |Autoclave; |Large scale 4.2: 0 °C / |Glovebox; |Autoclave; |Large scale 5.1: palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 0.92 h / 56 °C / |Inert atmosphere; |Large scale 5.2: 3.25 h / 56 °C / |Inert atmosphere; |Large scale 6.1: triethylamine / toluene / 0.17 h / 20 °C / |Inert atmosphere; |Large scale 7.1: N-ethyl-N,N-diisopropylamine; sodium azide / N,N-dimethyl-formamide / 70 °C / |Inert atmosphere; |Large scale 8.1: triphenylphosphine; water / toluene / 8 h / 70 °C / |Inert atmosphere; |Large scale 9.1: hydrogenchloride / isopropyl alcohol / |Inert atmosphere; |Large scale 10.1: 2,4,6-trichloro-1,3,5-triazine; 4-methyl-morpholine / acetonitrile / 4 h / 50 °C / |Inert atmosphere; |Large scale View Scheme

tetraethylammonium p-toluenesulfonate in N,N-dimethyl-formamide Ambient temperatureelectroreduction: Pb-cathode, carbon-rod anode, 15mA/cm-2;