potassium hydroxide in methanol; dichloromethane 2 h;

1: 96 percent / PdCl2(PPh3)2, CuI / diethylamine / 20 h / Ambient temperature 2: 1.) NaNO2, conc. HCl, 2.) KI / 1.) H2O, 0 deg C, 50 min, 2.) H2O, room temp., overnight 3: 73 percent / aq. NaOH / ethanol; tetrahydrofuran / 0.5 h View Scheme

1: 1.) NaNO2, conc. HCl, 2.) KI / 1.) H2O, 0 deg C, 50 min, 2.) H2O, room temp., overnight 2: 73 percent / aq. NaOH / ethanol; tetrahydrofuran / 0.5 h View Scheme

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: 96 percent / potassium carbonate / acetonitrile; H2O / 0.17 h / cooling 2.1: 93 percent / copper iodide; bis(triphenylphosphine)palladium(II) chloride; triethylamine / 3 h / 30 °C 3.1: 85 percent / methyl iodide / 96 h / 110 °C 4.1: 80 percent / potassium hydroxide / methanol; CH2Cl2 / 2 h View Scheme

1: 93 percent / copper iodide; bis(triphenylphosphine)palladium(II) chloride; triethylamine / 3 h / 30 °C 2: 85 percent / methyl iodide / 96 h / 110 °C 3: 80 percent / potassium hydroxide / methanol; CH2Cl2 / 2 h View Scheme

1: 85 percent / methyl iodide / 96 h / 110 °C 2: 80 percent / potassium hydroxide / methanol; CH2Cl2 / 2 h View Scheme

(i) PCl5, (ii) KOtBu, tBuOH; Multistep reaction;