AlCl3, aluminium chloride; bromine in tetrahydrofuran T=0°C; 0.5 h;

1: With magnesium sulfate; 3-chloro-benzenecarboperoxoic acid in chloroform T=20°C; 120 h; 2: With ammonium hydroxide in methanol; acetonitrile T=20°C; 3 h; Further stages.;

in methanol

1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere 3.1: palladium 10 on activated carbon; hydrogen / methanol / 1 h / 25 °C / 760.05 Torr 4.1: iodine; silver sulphate / methanol / 3 h / 25 °C 5.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 5.2: 3 h / -78 °C / Inert atmosphere View Scheme

1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: methanesulfonyl chloride; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere 3: palladium 10 on activated carbon; hydrogen / methanol / 1 h / 25 °C / 760.05 Torr 4: iodine; silver sulphate / methanol / 3 h / 25 °C View Scheme

1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere 3.1: palladium 10 on activated carbon; hydrogen / methanol / 1 h / 25 °C / 760.05 Torr 4.1: iodine; silver sulphate / methanol / 3 h / 25 °C 5.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 5.2: 3 h / -78 °C / Inert atmosphere 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; water; benzene / 24 h / Inert atmosphere; Reflux View Scheme

potassium carbonate; sodium iodide in (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide; N,N-dimethyl-formamide

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: 1.) Mg / 1.) ether, reflux, 0.5 h, 2.) ether, reflux, 2 h 2: 40 percent / TiCl3, LiAlH4 / 1,2-dimethoxy-ethane / 16 h / Heating 3: 1.) BBr3, 2.) 2N NaOH / 1.) CH2Cl2, RT, 4 h, 2.) CH2Cl2, MeOH View Scheme