1.1: Br2; potassium acetate / methanol / 1 h / 0 °C 1.2: 35 percent / aq. HBr / methanol / 20 °C 2.1: 94 percent / benzene / 1 h / Heating 3.1: 96 percent / H2 / Pd/C / methanol 4.1: 91 percent / lithium aluminum hydride / diethyl ether / 20 °C 5.1: 93 percent / pyridine / 3 h / -10 °C 6.1: 80 percent / potassium tert-butylate; dimethyl sulfoxide / 40 °C 7.1: potassium tert-butoxide; DMSO / 4 h / 60 °C View Scheme

1: 94 percent / benzene / 1 h / Heating 2: 96 percent / H2 / Pd/C / methanol 3: 91 percent / lithium aluminum hydride / diethyl ether / 20 °C 4: 93 percent / pyridine / 3 h / -10 °C 5: 80 percent / potassium tert-butylate; dimethyl sulfoxide / 40 °C 6: potassium tert-butoxide; DMSO / 4 h / 60 °C View Scheme

sodium hydride; dimethyl sulfoxide 1) 15 min, room temperature, 2) 60 - 68 deg C, 22 h; Multistep reaction;

in pentane T=23°C; Irradiation; Quantum yield;