N-chloro-succinimide; trifluorormethanesulfonic acid; palladium diacetate; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in 1,2-dichloro-ethane T=90°C; 6 h; Sealed tube; regioselective reaction;

sulfuric acid in benzene Cooling with iceReflux;

1: aq. KBrO3 / aq. H2SO4; acetic acid / 1.5 h / Heating 2: cc. H2SO4 View Scheme

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 22 h / 80 °C / |Inert atmosphere; |Schlenk technique 2: ammonium acetate; sodium periodate / acetone; water / 19 h / 20 °C View Scheme

1: With diisobutylaluminium hydride in tetrahydrofuran T=-78 - 20°C; 2 h; 2: With hydrogenchloride; water in tetrahydrofuran; diethyl ether