1: With n-butyllithium in diethyl ether; hexane T=-78°C; 2 h; 2: With copper(ll) bromide in diethyl ether; hexane T=-78°C; 1 h; 3: With nitrobenzene in diethyl ether; hexane T=20°C; 12 h;

1.1: bromine / dichloromethane; methanol / 20 °C / |Inert atmosphere 2.1: sodium nitrite; sulfuric acid / acetic acid / 4 h / 20 °C 2.2: 20 °C 3.1: n-butyllithium / hexane; diethyl ether / 2 h / -78 °C 3.2: 1 h / -78 °C 3.3: 12 h / 20 °C View Scheme

1.1: sodium nitrite; sulfuric acid / acetic acid / 4 h / 20 °C 1.2: 20 °C 2.1: n-butyllithium / hexane; diethyl ether / 2 h / -78 °C 2.2: 1 h / -78 °C 2.3: 12 h / 20 °C View Scheme