n-butyllithium; N,N,N',N,-tetramethylethylenediamine 1.) THF, 5-15 deg C, sonication, 2 h, 2.) r.t., several hours; Yield given. Multistep reaction. Yields of byproduct given;

1.1: 88 percent / aq. KOH / 1 h / Heating 2.1: n-BuLi / tetrahydrofuran / -78 °C 2.2: B(OMe)3 / tetrahydrofuran / -78 - 20 °C 3.1: 100 percent / aq. Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; ethanol / 42 h / Heating 4.1: 81 percent / aq. CAN / acetonitrile / 0.08 h / 20 °C 5.1: 82 percent / t-BuOK / dimethylformamide / 0.17 h / 80 °C / Irradiation View Scheme

1.1: 88 percent / aq. KOH / 1 h / Heating 2.1: n-BuLi / tetrahydrofuran / -78 °C 2.2: B(OMe)3 / tetrahydrofuran / -78 - 20 °C 3.1: 100 percent / aq. Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; ethanol / 42 h / Heating 4.1: 87 percent / t-BuOK / dimethylformamide / 80 °C / Irradiation View Scheme

1: 95 percent / imidazole / dimethylformamide 3: pyridiniumchlorochromate / CH2Cl2 / 25 °C View Scheme

hydrogenchloride; tin(ll) chloride in ethanol

1: sodium acetate; acetic acid; bromine / Lichtausschluss 2: ethanol; SnCl2; concentrated aqueous HCl View Scheme

1: tin (II)-chloride; glacial acetic acid 2: iron (III)-chloride; acetic acid 3: glacial acetic acid; bromine / im Dunkeln 4: zinc; hydrochloric acid; alcoholic diethyl ether View Scheme

1: iron (III)-chloride; acetic acid 2: glacial acetic acid; bromine / im Dunkeln 3: zinc; hydrochloric acid; alcoholic diethyl ether View Scheme

1: concentrated sulfuric acid 2: zinc; hydrochloric acid; alcoholic diethyl ether View Scheme

1.1: 88 percent / aq. KOH / 1 h / Heating 2.1: n-BuLi / tetrahydrofuran / -78 °C 2.2: B(OMe)3 / tetrahydrofuran / -78 - 20 °C 3.1: 100 percent / aq. Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; ethanol / 42 h / Heating View Scheme