n-butyllithium in tetrahydrofuran; hexane

potassium hydroxide in methanol; dichloromethane 0.75 h;

1: 1) Mg, 2) CuBr*Me2S / y / 1) THF, reflux, 90 min, 2) reflux, 20 h 2: 69 percent / Br2, Fe / CCl4 / 1.5 h 3: 1) n-butyllithium, 2) I2 / 1) THF, hexane, -78 deg C, 30 min, 2) to RT overnight 4: 81 percent / triphenylphosphine, PdCl2, Et3N, CuI / tetrahydrofuran / 0.33 h / Ambient temperature 5: 94 percent / KOH / methanol; CH2Cl2 / 0.75 h View Scheme

1: 1) Mg, 2) CuBr*Me2S / y / 1) THF, reflux, 90 min, 2) reflux, 20 h 2: 69 percent / Br2, Fe / CCl4 / 1.5 h 3: 1) n-butyllithium, 2) I2 / 1) THF, hexane, -78 deg C, 30 min, 2) to RT overnight 4: 81 percent / triphenylphosphine, PdCl2, Et3N, CuI / tetrahydrofuran / 0.33 h / Ambient temperature 5: 94 percent / KOH / methanol; CH2Cl2 / 0.75 h View Scheme

1: Sonogashira Cross-Coupling; 5 h; 2: With sodium hydride in toluene T=110°C;

1: 69 percent / Br2, Fe / CCl4 / 1.5 h 2: 1) n-butyllithium, 2) I2 / 1) THF, hexane, -78 deg C, 30 min, 2) to RT overnight 3: 81 percent / triphenylphosphine, PdCl2, Et3N, CuI / tetrahydrofuran / 0.33 h / Ambient temperature 4: 94 percent / KOH / methanol; CH2Cl2 / 0.75 h View Scheme

1: 1) n-butyllithium, 2) I2 / 1) THF, hexane, -78 deg C, 30 min, 2) to RT overnight 2: 81 percent / triphenylphosphine, PdCl2, Et3N, CuI / tetrahydrofuran / 0.33 h / Ambient temperature 3: 94 percent / KOH / methanol; CH2Cl2 / 0.75 h View Scheme

1: 81 percent / triphenylphosphine, PdCl2, Et3N, CuI / tetrahydrofuran / 0.33 h / Ambient temperature 2: 94 percent / KOH / methanol; CH2Cl2 / 0.75 h View Scheme

potassium hydroxide; phosphorus pentachloride; phosphorus trichoride 1) reflux, 48 h; 2) ethanol, reflux, 40 h; Yield given. Multistep reaction;