tetra-(n-butyl)ammonium iodide; potassium carbonate in acetone

hydrogenchloride

pyridine hydrochloride T=180 - 200°C; 1.5 h;

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / |Inert atmosphere 2: AlCl3, aluminium chloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 3: sodium hydride / paraffin oil / 90 °C / |Inert atmosphere 4: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / |Inert atmosphere 5: pyridinium p-toluenesulfonate / toluene / |Inert atmosphere; |Reflux; |Dean-Stark 6: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 7: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 8: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 9: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 10: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 11: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: LiAlH4 / diethyl ether 2: PBr3 / benzene 3: (i) Mg, Et2O, THF, (ii) /BRN= 1900390/ 4: aq. H3PO4, P2O5 View Scheme

1: LiAlH4 / diethyl ether 2: PBr3 / benzene 3: (i) Mg, Et2O, THF, (ii) /BRN= 1900390/ View Scheme

1: SOCl2 2: NaN3 / acetone; H2O 3: benzene / Heating View Scheme

1: benzene; thionyl chloride 2: aqueous acetone; sodium azide 3: benzene 4: aqueous hydrochloric acid View Scheme

1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 20 °C 2: AlCl3, aluminium chloride / dichloromethane / 2 h / 20 °C 3: sodium hydride / paraffin oil / 90 °C View Scheme

ammonia T=200 - 230°C;