hydrogenchloride in 1,4-dioxane 0.5 h; Heating;

hydrogenchloride in methanol 0.333333 h; Heating;

in methanol 5 h; Heating;

in methanol 168 h; Heating;

1: 78 percent / Br2, AcOH / 0.5 h / Ambient temperature 2: 75 percent / 18 h / Heating 3: 81 percent / Et4NCl, Pd(PPh3)2Cl2 / acetonitrile / 24 h / Heating 4: 96 percent / concd. HCl / methanol / 0.33 h / Heating View Scheme

1: 75 percent / 18 h / Heating 2: 81 percent / Et4NCl, Pd(PPh3)2Cl2 / acetonitrile / 24 h / Heating 3: 96 percent / concd. HCl / methanol / 0.33 h / Heating View Scheme

1: 81 percent / Et4NCl, Pd(PPh3)2Cl2 / acetonitrile / 24 h / Heating 2: 96 percent / concd. HCl / methanol / 0.33 h / Heating View Scheme

1: 1.) 25percent HCl, NaNO2; 2.) CuCl / 1.) H2O, 5 deg C, 15 min 2.) 80 deg C, 15 min 2: 94 percent / methanol / 168 h / Heating View Scheme

1: 95 percent / NaH / tetrahydrofuran / 1.) r.t., 1 h, 2.) r.t., 1 h 2: 55 percent / t-BuLi / tetrahydrofuran; pentane / 1.) -78 deg C, 0.5 h, 2.) -78 deg C, 2 h 3: 91 percent / KOH / tetrahydrofuran; methanol / 2 h / Ambient temperature 4: 86 percent / I2, KOH / dimethylformamide / 2 h / Ambient temperature 5: 1.) propane-1,3-diol, MgSO4, 2.) K3PO4 / 2.) <Pd(PPh3)4> / 1.) C6H6, r.t., 24 h, 2.) DMF, 6 h 6: 41 percent / BBr3 / 1,2-dichloro-ethane / 24 h / Heating View Scheme

1: 67 percent / benzyltriethylammoniumchloride, 50percent NaOH / CH2Cl2 / 0.17 h 2: 60 percent / HBr/glacial acetic acid / tetrahydrofuran / Heating View Scheme