caesium carbonate in methanol T=20°C; 0.0833333 h; Inert atmosphere;

potassium hydroxide in methanol; dichloromethane 2 h;

1.1: 6 M HCl / acetonitrile / 0.25 h / 70 °C 1.2: aq. sodium nitrite / H2O; acetonitrile / 0.25 h / 15 °C 1.3: 92 percent / potassium carbonate / acetonitrile; H2O / 0.17 h / cooling 2.1: 91 percent / copper iodide; bis(triphenylphosphine)palladium(II) chloride; triethylamine / 3 h / 30 °C 3.1: 90 percent / methyl iodide / 96 h / 110 °C 4.1: 87 percent / potassium hydroxide / methanol; CH2Cl2 / 2 h View Scheme

1: 1.) NaNO2, conc. HCl, 2.) KI / 1.) H2O, 0 deg C, 50 min, 2.) H2O, room temp., overnight 2: 80 percent / aq. NaOH / ethanol; tetrahydrofuran / 0.5 h View Scheme

1: 91 percent / copper iodide; bis(triphenylphosphine)palladium(II) chloride; triethylamine / 3 h / 30 °C 2: 90 percent / methyl iodide / 96 h / 110 °C 3: 87 percent / potassium hydroxide / methanol; CH2Cl2 / 2 h View Scheme

1: 90 percent / methyl iodide / 96 h / 110 °C 2: 87 percent / potassium hydroxide / methanol; CH2Cl2 / 2 h View Scheme

iodine; magnesium bromide 2.) THF,-60 deg C, 30 deg C; Yield given. Multistep reaction;

n-butyllithium; potassium tert-butylate; iodine; magnesium bromide Multistep reaction;

copper(l) iodide; triphenylphosphine; potassium carbonate in N,N-dimethyl-formamide T=160°C; 24 h;