n-butyllithium in tetrahydrofuran T=-78 - 20°C;

in acetonitrile T=20°C; 2 h; RefluxInert atmosphere;

1.1: bromine / methanol / 2 h / -5 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C 2.1: sodium iodide / acetone / 4 h / 20 °C / Inert atmosphere 3.1: acetonitrile / 2 h / 20 °C / Reflux; Inert atmosphere View Scheme

1.1: methanol; sodium / 1 h / 20 °C / Reflux; Inert atmosphere 1.2: 21 h / 20 °C / Reflux; Inert atmosphere 2.1: bromine / methanol / 2 h / -5 - 20 °C / Inert atmosphere 2.2: 1 h / 20 °C 3.1: sodium iodide / acetone / 4 h / 20 °C / Inert atmosphere 4.1: acetonitrile / 2 h / 20 °C / Reflux; Inert atmosphere View Scheme