N-bromosuccinmide in dichloromethane 24 h; Irradiation;

1: 1) Mg / 2) NiCl2(PPh3)2 / 1) Et2O, 2h, reflux, 2) Et2O, 16h, reflux 2: NBS, benzoylperoxide / CCl4 / 3 h / Heating View Scheme

1: 74 percent / conc. H2SO4, H5IO6, I2, glacial HOAc / H2O / 3 h / 70 °C 2: 1) Mg / 2) NiCl2(PPh3)2 / 1) Et2O, 2h, reflux, 2) Et2O, 16h, reflux 3: NBS, benzoylperoxide / CCl4 / 3 h / Heating View Scheme

N-bromosuccinmide; meta-chloroperoxybenzoic acid in tetrachloromethane 3 h; Heating; Yield given. Yields of byproduct given;

1: acetic acid / 22 h / Heating 2: 87 percent / 15percent NaOH / methanol / 6 h / 50 °C 3: 48 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 4: 1) PhLi / 1) THF, benzene, Et2O, -70 deg C, 2a) THF, -50 deg C, 2 h, 2b) -50 to -10 deg C, 1 h 5: 64 percent / benzene / 144 h / Irradiation 6: 75 percent / DDQ / benzene / 48 h / Heating View Scheme