1: p-chlorobenzenethiol With sodium hydride in N,N-dimethyl-formamide Metallation; 1 h; 2: 1-chloro-4-(difluoroiodomethylsulfanyl)benzene in N,N-dimethyl-formamide T=20°C; Substitution; 1 h;

silver hexafluoroantimonate in dichloromethane T=-78°C; 0.666667 h; Inert atmosphereSchlenk technique;

silver hexafluoroantimonate in dichloromethane T=-78°C; Inert atmosphereSchlenk technique;

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -78 - 20 °C / |Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / |Inert atmosphere 2.1: silver hexafluoroantimonate / dichloromethane / 0.67 h / -78 °C / |Inert atmosphere; |Schlenk technique View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -78 - 20 °C / |Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / |Inert atmosphere 2.1: silver hexafluoroantimonate / dichloromethane / -78 °C / |Inert atmosphere; |Schlenk technique View Scheme

sodium hydride DMF, -40 deg C; Yield given. Multistep reaction;

sodium hydride in N,N-dimethyl-formamide T=20°C; Substitution; Reduction; 5 h; Product distribution; Further Variations:ReagentsSolventsratio of reagents;