1.1: NaH / tetrahydrofuran / 0 - 20 °C 1.2: 80 percent / tetrahydrofuran / Heating 2.1: CH2Cl2 / 1.5 h / 0 - 20 °C 3.1: H2O / acetone / 1 h / 20 °C View Scheme

potassium tert-butylate in tetrahydrofuran T=75°C;

carbon tetrabromide; triphenylphosphine in dichloromethane T=-10°C;

1: 1-Bromo-11-hydroxyundecane With 1,10-phenanthroline; potassium tert-butylate; copper(l) chloride in o-di-fluorobenzene T=20°C; 0.166667 h; Inert atmosphere; 2: With 1-methyl-1H-imidazole; di-tert-butylazodicarboxylate; oxygen in o-di-fluorobenzene Reflux; 3: diazomethyl-trimethyl-silane With triphenylphosphine; isopropyl alcohol in o-di-fluorobenzene; diethyl ether T=60°C; Inert atmosphere;

in tetrahydrofuran T=0°C; Wittig reaction;

2,2,4-trimethylpentane; tetradecafluorohexane; bromine T=20°C; 2 h; Irradiation;

1: 80 percent / PCC / CH2Cl2 / 3 h / 20 °C 2: 75 percent / tetrahydrofuran / 0 °C View Scheme

1.1: iodine; hydrogen bromide / toluene / 30 h / 80 °C / |Dean-Stark 2.1: toluene-4-sulfonic acid / dichloromethane / 5 h / 0 - 20 °C 3.1: iodine; magnesium / tetrahydrofuran / 5.33 h / 20 °C / |Inert atmosphere; |Reflux 3.2: 12 h / 20 - 80 °C / |Ionic liquid 4.1: pyridinium p-toluenesulfonate / methanol / 50 °C 5.1: triphenylphosphine; carbon tetrabromide / dichloromethane / -10 °C View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 5 h / 0 - 20 °C 2.1: iodine; magnesium / tetrahydrofuran / 5.33 h / 20 °C / |Inert atmosphere; |Reflux 2.2: 12 h / 20 - 80 °C / |Ionic liquid 3.1: pyridinium p-toluenesulfonate / methanol / 50 °C 4.1: triphenylphosphine; carbon tetrabromide / dichloromethane / -10 °C View Scheme

1.1: iodine; magnesium / tetrahydrofuran / 5.33 h / 20 °C / |Inert atmosphere; |Reflux 1.2: 12 h / 20 - 80 °C / |Ionic liquid 2.1: pyridinium p-toluenesulfonate / methanol / 50 °C 3.1: triphenylphosphine; carbon tetrabromide / dichloromethane / -10 °C View Scheme