1: thionyl chloride / CH2Cl2 / 6 h / Heating 2: 38 percent / 1,4-dicyanobenzene / acetonitrile / 10 °C / Irradiation 3: 1,4-dicyanobenzene / methanol; acetonitrile / 10 °C / Irradiation View Scheme

thionyl chloride in dichloromethane 6 h; Heating; Yield given;