1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere 1.2: 24 h / -78 - 20 °C / Inert atmosphere 1.3: 0.33 h / 0 °C 2.1: sodium hydroxide / benzene / 20 h / 20 °C 3.1: 0.5 h / 200 °C / neat (no solvent, solid phase) 4.1: bromine; sodium sulfite / chloroform; water / 0 - 20 °C / Inert atmosphere View Scheme

sulfuric acid; iodine; periodic acid in water; acetic acid T=70°C; 5 h;

1: 66 percent / I2; KIO3; AcOH / CCl4 / Heating 2: piperidine; Pd(PPh3)4; CuI 3: K2CO3; methanol / tetrahydrofuran 4: piperidine; Pd(PPh3)4; CuI 5: tetrabutylammonium fluoride / tetrahydrofuran View Scheme

1: 66 percent / I2; KIO3; AcOH / CCl4 / Heating 2: piperidine; Pd(PPh3)4; CuI 3: K2CO3; methanol / tetrahydrofuran 4: piperidine; Pd(PPh3)4; CuI 5: tetrabutylammonium fluoride / tetrahydrofuran View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere 1.2: 24 h / -78 - 20 °C / Inert atmosphere 1.3: 0.33 h / 0 °C 2.1: sodium hydroxide / benzene / 20 h / 20 °C 3.1: 0.5 h / 200 °C / neat (no solvent, solid phase) View Scheme