1: 1.) nBuLi / 1.) THF, r.t.; 2.) r.t. 2: 87 percent / 25percent HCl / Heating View Scheme

1: 1.) n-BuLi, TMEDA, 2.) I2 / 1.) THF, hexane, 0 deg C, 2 h, 2.) THF, hexane, 0 deg C, 2 h 2: 93 percent / Pd(OAc)2, Et3N / acetonitrile / 48 h / Heating 3: 87 percent / 3M aq. HCl / 48 h / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -10 - 20 °C / Inert atmosphere 1.2: 2 h / -10 - 20 °C / Inert atmosphere 2.1: hydrogen bromide / 120 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C 1.2: -78 - 20 °C 1.3: -78 - 20 °C 2.1: hydrogenchloride; water / 1,4-dioxane / 6 h / Reflux View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C 1.2: -78 - 20 °C 1.3: -78 - 20 °C 2.1: hydrogenchloride; water / 1,4-dioxane / 6 h / Reflux 3.1: sodium nitrite / 1,4-dioxane / -5 °C 3.2: -5 - 80 °C View Scheme

1: 1.) nBuLi / 1.) THF, r.t.; 2.) r.t. 2: 87 percent / 25percent HCl / Heating 3: 92 percent / acetone / Ambient temperature View Scheme

Multi-step reaction with 11 steps 1: 1.) nBuLi / 1.) THF, r.t.; 2.) r.t.2: 87 percent / 25percent HCl / Heating3: 92 percent / acetone / Ambient temperature4: 97 percent / N-bromosuccinimide / dimethylformamide / Ambient temperature5: 1.) NaNO2, 20percent HCl / 1.) 0 deg C; 2.) H2O, 65 deg C6: 91 percent / tetrahydrofuran / Ambient temperature7: 1.) 49percent HF; 2.) MnO2 / 1.) THF, r.t.; 2.) CH2Cl2, reflux8: pyridine, 4-dimethylaminopyridine / ethyl acetate / Ambient temperature9: 97 percent / tetrahydrofuran / Ambient temperature10: 1.) zinc, acetic acid / 1.) 80 deg C; 2.) Me2CO, r.t.11: 44 percent / tetrakis(triphenylphosphine)palladium  

Multi-step reaction with 11 steps 1: 1.) nBuLi / 1.) THF, r.t.; 2.) r.t.2: 87 percent / 25percent HCl / Heating3: 92 percent / acetone / Ambient temperature4: 97 percent / N-bromosuccinimide / dimethylformamide / Ambient temperature5: 1.) NaNO2, 20percent HCl / 1.) 0 deg C; 2.) H2O, 65 deg C6: 91 percent / tetrahydrofuran / Ambient temperature7: 1.) 49percent HF; 2.) MnO2 / 1.) THF, r.t.; 2.) CH2Cl2, reflux8: pyridine, 4-dimethylaminopyridine / ethyl acetate / Ambient temperature9: 97 percent / tetrahydrofuran / Ambient temperature10: 1.) zinc, acetic acid / 1.) 80 deg C; 2.) Me2CO, r.t.11: 66 percent / tetrakis(triphenylphosphine)palladium  

With  hydrogenchloride in  tetrahydrofuran; hexane Show Experimental Procedure