1: NaHCO3 / diethyl ether / 2 h / Ambient temperature 2: phosphoryl chloride / benzene / 2 h / Heating 3: 100 percent / 1,2-dichloro-benzene / 1 h / 180 °C 4: 62 percent / NaBH4 / methanol / Ambient temperature View Scheme

oxalyl dichloride in dichloromethane 1 h; Heating;

1: 65 percent / Na acetate, Br2 / acetic acid / Ambient temperature 2: 62 percent / NaNH2, NH4Cl / tetrahydrofuran / 2 h / Ambient temperature 3: 98.5 percent / KOH, H2O / ethanol / 3 h / Heating 4: oxalyl chloride / CH2Cl2 / 1 h / Heating View Scheme

1: 62 percent / NaNH2, NH4Cl / tetrahydrofuran / 2 h / Ambient temperature 2: 98.5 percent / KOH, H2O / ethanol / 3 h / Heating 3: oxalyl chloride / CH2Cl2 / 1 h / Heating View Scheme

1: 98.5 percent / KOH, H2O / ethanol / 3 h / Heating 2: oxalyl chloride / CH2Cl2 / 1 h / Heating View Scheme