in methanol; acetonitrile T=-10 - 25°C; 3 h;

in dichloromethane T=-15 - 20°C;

1: 91 percent / NaNO2, Na2CO3, H2SO4 / H2O / 0.5 h / -10 °C 2: 78 percent / H2O / 4 h / 0 °C 3: 90 percent / PCl5 / 1.) 150 deg C, 1 h, 2.) C6H6, reflux, 3 h 5: 74 percent / acetonitrile; methanol / 3 h / -10 - 25 °C View Scheme

1: 78 percent / H2O / 4 h / 0 °C 2: 90 percent / PCl5 / 1.) 150 deg C, 1 h, 2.) C6H6, reflux, 3 h 4: 74 percent / acetonitrile; methanol / 3 h / -10 - 25 °C View Scheme

Yield given. Multistep reaction;