1: With n-butyllithium in tetrahydrofuran T=-78°C; 3 h; Inert atmosphere; 2: With boric acid trimethyl ester in tetrahydrofuran T=-78°C; Inert atmosphere; 3: With hydrogenchloride in tetrahydrofuran; water T=-78 - 0°C; 3 h; Inert atmosphere;

1.1: 82 percent / NaOH / dimethylsulfoxide / 90 °C 2.1: 96 percent / NBS / acetone / 3 h / 80 °C 3.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 3.2: 81 percent / trimethyl borate / tetrahydrofuran / 2 h / -78 °C View Scheme

1.1: 96 percent / NBS / acetone / 3 h / 80 °C 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: 81 percent / trimethyl borate / tetrahydrofuran / 2 h / -78 °C View Scheme

1.1: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 60 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere 2.2: -78 °C / Inert atmosphere 2.3: 3 h / -78 - 0 °C / Inert atmosphere View Scheme

CH3CH2CH2CH2Li; H3O(1+) in tetrahydrofuran reaction of aryl bromide with butyllithium in THF at -78°C, treatment with boron compd. at -78°C, acidic hydrolysis;