lithium diethylamide in ethylene glycol dimethyl ether T=-45°C; 2.41667 h; Inert atmosphere;

1: sodium carbonate / tert-butyl methyl ether; water / 1 h / 15 - 25 °C / |Inert atmosphere 2: lithium diisopropyl amide / ethylene glycol dimethyl ether; tetrahydrofuran / 1 h / -35 - 0 °C / |Inert atmosphere 3: potassium carbonate; triphenylphosphine; palladium diacetate / water; ethylene glycol dimethyl ether; tetrahydrofuran / 8 h / 70 °C / |Inert atmosphere 4: lithium diethylamide / ethylene glycol dimethyl ether / 2.42 h / -45 °C / |Inert atmosphere View Scheme

1: lithium diisopropyl amide / ethylene glycol dimethyl ether; tetrahydrofuran / 1 h / -35 - 0 °C / |Inert atmosphere 2: potassium carbonate; triphenylphosphine; palladium diacetate / water; ethylene glycol dimethyl ether; tetrahydrofuran / 8 h / 70 °C / |Inert atmosphere 3: lithium diethylamide / ethylene glycol dimethyl ether / 2.42 h / -45 °C / |Inert atmosphere View Scheme

1: potassium carbonate; triphenylphosphine; palladium diacetate / water; ethylene glycol dimethyl ether; tetrahydrofuran / 8 h / 70 °C / |Inert atmosphere 2: lithium diethylamide / ethylene glycol dimethyl ether / 2.42 h / -45 °C / |Inert atmosphere View Scheme

1: With bromine in ethylene glycol dimethyl ether T=15 - 45°C; 4.33333 h; 2: With water; sodium carbonate in ethylene glycol dimethyl ether T=50 - 55°C; 5 h; Product distribution / selectivity;