sodium nitrite in ethanol; water; toluene

sodium azide; tributyltin chloride in o-xylene T=25 - 143°C;

1: With methoxybenzene; trifluoroacetic acid T=20 - 80°C; 13 h; 2: With potassium hydroxide in water; toluene

manganese(IV) oxide in water T=80 - 180°C; 0.833333 h; microwave irradiation;

hydrogenchloride in tetrahydrofuran T=25°C; 4 h;

1: tetrabutylammomium bromide; potassium carbonate / chloroform; water / 2 h / 10 - 55 °C 2: 1-methyl-pyrrolidin-2-one; [Ru(COD)(Cl2)]2; triphenylphosphine / 2 h / 140 °C 3: methanol; sodium methylate / 1.5 h / 20 °C 4: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 5: potassium carbonate / N,N-dimethyl acetamide / 8 h / -10 - 20 °C 6: methoxybenzene; trifluoroacetic acid / 13 h / 20 - 80 °C View Scheme

1: 1-methyl-pyrrolidin-2-one; [Ru(COD)(Cl2)]2; triphenylphosphine / 2 h / 140 °C 2: methanol; sodium methylate / 1.5 h / 20 °C 3: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 4: potassium carbonate / N,N-dimethyl acetamide / 8 h / -10 - 20 °C 5: methoxybenzene; trifluoroacetic acid / 13 h / 20 - 80 °C View Scheme

1.1: phosphorus pentachloride / dichloromethane / 1.18 h / -16 - 17 °C 1.2: 8.2 h / -10 - 20 °C 2.1: 1-methyl-pyrrolidin-2-one; [Ru(COD)(Cl2)]2; triphenylphosphine / 2 h / 140 °C 3.1: methanol; sodium methylate / 1.5 h / 20 °C 4.1: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 5.1: potassium carbonate / N,N-dimethyl acetamide / 8 h / -10 - 20 °C 6.1: methoxybenzene; trifluoroacetic acid / 13 h / 20 - 80 °C View Scheme

1.1: triethylamine / tetrahydrofuran / 3 h / 16 - 20 °C 2.1: phosphorus pentachloride / dichloromethane / 1.18 h / -16 - 17 °C 2.2: 8.2 h / -10 - 20 °C 3.1: 1-methyl-pyrrolidin-2-one; [Ru(COD)(Cl2)]2; triphenylphosphine / 2 h / 140 °C 4.1: methanol; sodium methylate / 1.5 h / 20 °C 5.1: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 6.1: potassium carbonate / N,N-dimethyl acetamide / 8 h / -10 - 20 °C 7.1: methoxybenzene; trifluoroacetic acid / 13 h / 20 - 80 °C View Scheme

1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 3: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 4: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 5: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 6: 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme