hydrogenchloride in acetic acid T=20°C; 22 h;

1.1: 58.1 percent / potassium carbonate; potassium iodide / dimethylformamide / 24 h / 150 °C 2.1: t-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 68 percent / tetrahydrofuran / -78 - 20 °C 3.1: 94 percent / hydrochloric acid / acetic acid / 22 h / 20 °C View Scheme

1.1: 98 percent / boron tribromide / CH2Cl2 / 1 h / 0 °C 2.1: 58.1 percent / potassium carbonate; potassium iodide / dimethylformamide / 24 h / 150 °C 3.1: t-butyllithium / tetrahydrofuran / 1 h / -78 °C 3.2: 68 percent / tetrahydrofuran / -78 - 20 °C 4.1: 94 percent / hydrochloric acid / acetic acid / 22 h / 20 °C View Scheme

1.1: 58.1 percent / potassium carbonate; potassium iodide / dimethylformamide / 24 h / 150 °C 2.1: t-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 68 percent / tetrahydrofuran / -78 - 20 °C 3.1: 94 percent / hydrochloric acid / acetic acid / 22 h / 20 °C View Scheme

1.1: t-butyllithium / tetrahydrofuran / 1 h / -78 °C 1.2: 68 percent / tetrahydrofuran / -78 - 20 °C 2.1: 94 percent / hydrochloric acid / acetic acid / 22 h / 20 °C View Scheme