copper(l) chloride in methanol; N,N-dimethyl-formamide T=110°C; 8 h; Inert atmosphere;

1.1: palladium diacetate; triethylamine; triphenylphosphine / 72 h / 120 °C / Inert atmosphere 1.2: 3 h / 25 °C 2.1: iodine / 1 h / 25 °C 3.1: dihydrogen peroxide; toluene-4-sulfonic acid / acetic acid / 0.42 h / 75 °C 4.1: sodium carbonate / methanol; water / 20 h / 25 °C View Scheme

1: n-butyllithium / tetrahydrofuran / -78 °C / |Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethylene glycol dimethyl ether; water / |Inert atmosphere; |Reflux View Scheme

dihydrogen peroxide; acetic acid; sodium bromide in water T=40°C; 2 h;

bromine; sodium acetate; acetic acid in tetrachloromethane T=10 - 20°C; 2.5 h; Inert atmosphere;

1: 90 percent / triphenylphosphine, N-bromosuccinimide / CH2Cl2 / 1 h / 0 °C 2: 1.) lithium triethylborohydride, 2.) 20percent NaOH, 30percent H2O2 / 1.) THF, RT, 30 min View Scheme

sodium hydroxide; dihydrogen peroxide; lithium triethylborohydride 1.) THF, RT, 30 min; Yield given. Multistep reaction;

1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethylene glycol dimethyl ether; water / |Inert atmosphere; |Reflux 2: sodium acetate; acetic acid; bromine / tetrachloromethane / 2.5 h / 10 - 20 °C / |Inert atmosphere View Scheme