hydrogenchloride; N,N,N',N',N'',N''-hexamethylphosphoric triamide in N-methyl-acetamide; acetonitrile

hydrogenchloride; N,N,N',N',N'',N''-hexamethylphosphoric triamide in acetonitrile

potassium chloride; tetra-n-butylammonium acetate; potassium carbonate; palladium diacetate in N,N-dimethyl-formamide T=90°C; 1.5 h;

potassium hydroxide; acetic anhydride 1) MeOH, 0 deg C to 5 deg C, 2 h, 2) MeOH, 100 deg C, 30 min; Yield given. Multistep reaction;

2,9-dimethyl-1,10-phenanthroline; palladium diacetate; p-benozquinone in acetonitrile T=100°C; Heck reaction; 0.5 h; Microwave irradiation;

1: tin(IV) chloride; pyridine 1-oxide / dichloromethane / 4 h / -78 °C 2: Dess-Martin periodane / dichloromethane / 20 °C 3: tetrakis-(ethylene)-μ,μ'-dichlorodirhodium(I); potassium hydroxide; (2,6-bis((R)-tert-butylsulfinyl)phenyl)diphenylphosphine / dichloromethane; water / 12 h / 20 °C / |Glovebox; |Schlenk technique 4: hydrazine hydrate / methanol / 4 h / |Reflux 5: sodium hydride / water; dimethyl sulfoxide / 120 °C 6: hydrogenchloride; water / 20 h / |Reflux 7: chlorosulfonic acid / dichloromethane / 0.75 h / 20 °C View Scheme

1: benzene-1,4-diol / benzene / 96 h / 180 °C 2: H2 / Pd-C / ethyl acetate 3: (i) CuBr2, AcOEt, CHCl3, (ii) Li2CO3, LiBr, DMF View Scheme