thionyl chloride; N,N-dimethyl-formamide in chloroform 1 h; Heating;

1: 60 percent / SO2Cl2 / CHCl3 / 0.5 h / Heating 2: SOCl2 / 0.23 h / Heating View Scheme

1: 61 percent / sulfuryl chloride / diethyl ether / 2 h / Ambient temperature 2: 90 percent / K2CO3 / acetone / 16 h / Ambient temperature 3: 78 percent / KOH / H2O; dimethylsulfoxide / 24 h / 80 - 90 °C 4: SOCl2 / toluene / 2 h / Heating View Scheme

1: 78 percent / KOH / H2O; dimethylsulfoxide / 24 h / 80 - 90 °C 2: SOCl2 / toluene / 2 h / Heating View Scheme

1: 90 percent / K2CO3 / acetone / 16 h / Ambient temperature 2: 78 percent / KOH / H2O; dimethylsulfoxide / 24 h / 80 - 90 °C 3: SOCl2 / toluene / 2 h / Heating View Scheme

1: 3.13 g / CH2Cl2 / 20 °C 2: 71 percent / BBr3 / CH2Cl2 / -20 - 20 °C View Scheme

in butanone 2 h; Ambient temperature; Yield given;