1.1: sodium nitrite; HCl / H2O / 5 h / 0 °C 1.2: 72 percent / KI / H2O / 0.17 h / 90 °C 2.1: thionyl chloride; N,N-dimethylformamide / 2 h / Heating 3.1: AlCl3 / 1 h / Heating 4.1: 49 percent / Heating View Scheme

Heating;

1: thionyl chloride; N,N-dimethylformamide / 2 h / Heating 2: AlCl3 / 1 h / Heating 3: 49 percent / Heating View Scheme

1: AlCl3 / 1 h / Heating 2: 49 percent / Heating View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / -10 °C 1.2: hexane; tetrahydrofuran / 3 h / 0 - 20 °C 2.1: potassium hydroxide / methanol / 0.25 h / 0 - 20 °C 3.1: 56 percent / acidic alumina / toluene / 1.5 h / Heating View Scheme