1: methyllithium With copper (I) cyanide in diethyl ether T=-50°C; 0.5 h; Inert atmosphere; 2: C14H15F3O5S in diethyl ether T=-50°C; 0.5 h; Inert atmosphere;

in tetrahydrofuran 24 h; RefluxInert atmosphereSchlenk technique;

1.1: sodium hydride / mineral oil; toluene / 1.5 h / 85 °C 1.2: 2 h / 0 °C 2.1: copper (I) cyanide / diethyl ether / 0.5 h / -50 °C / |Inert atmosphere 2.2: 0.5 h / -50 °C / |Inert atmosphere View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C / |Inert atmosphere 2.1: sodium hydride / mineral oil; toluene / 1.5 h / 85 °C 2.2: 2 h / 0 °C 3.1: copper (I) cyanide / diethyl ether / 0.5 h / -50 °C / |Inert atmosphere 3.2: 0.5 h / -50 °C / |Inert atmosphere View Scheme

1: methanesulfonic acid; zinc / tetrahydrofuran / 1.5 h / |Reflux; |Inert atmosphere; |Schlenk technique 2: tetrahydrofuran / 24 h / |Reflux; |Inert atmosphere; |Schlenk technique View Scheme

iodine in benzene 528 h; Heating; Title compound not separated from byproducts;

sodium ethanolate 1.) ethanol, 30 min, 2.) reflux, 24h; Yield given. Multistep reaction. Yields of byproduct given;

lithium hydroxide hydrate; water in tetrahydrofuran; methanol T=20 - 70°C;