1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 3: 73 percent / silica gel / tetrahydrofuran; H2O / 5 h / 25 °C 4: 22 percent / hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 5: 92 percent / 5percent aq. HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1a) Mg / 1b) (tpp)2NiCl2 / 1a) ether, 30 deg C, 1 h, 1b) benzene, 10 min, 2) r.t., 72 h 2: 1) trifluoroacetic anhydride, 2) LiBr / 1) THF, 0-5 deg C, 45 min, 2) THF, DMF, 80 deg C, overnight 3: 1) Mg, 2) LiCuCl4 / 1) ether, 2 h, 2) THF, 0 deg C, 3.75 h View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 3: 73 percent / silica gel / tetrahydrofuran; H2O / 5 h / 25 °C 4: 22 percent / hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 5: 92 percent / 5percent aq. HCl / tetrahydrofuran / 1 h / Ambient temperature 6: 86 percent / pyridine / 5 h / 0 °C View Scheme

1: acetic acid / Heating 2: KOH / methanol View Scheme

N-bromosuccinmide; triphenylphosphine in DMF (N,N-dimethyl-formamide) T=20°C; 0.5 h;

carbon tetrabromide; triphenylphosphine in dichloromethane Ambient temperature;

1: 90 percent / quinoline, H2 / Lindlar's catalyst / hexane 2: 80 percent / PBr3, pyridine / diethyl ether / 2 h / Heating View Scheme

1: 100 percent / pyridine, H2 / 5percent Pd/CaCO3 with 3.5percent lead / methanol 2: 88 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature View Scheme

sodium bromide in N,N-dimethyl-formamide T=75°C; 2 h; Title compound not separated from byproducts;

in acetic acid Heating;