hydrogenchloride in water 24 h; Heating;

1: With sodium hydride in tetrahydrofuran; N,N-dimethyl-formamide T=0°C; 0.333333 h; 2: With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in tetrahydrofuran; N,N-dimethyl-formamide T=0 - 20°C; Further stages.;

1: With sodium hydride in N,N-dimethyl-formamide T=0 - 20°C; 1.41667 h; 2: With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in N,N-dimethyl-formamide T=0 - 20°C;

perchloryl fluoride; potassium tert-butylate in toluene 0.833333 h; temperature below 22 deg C;

phosphorous acid diethyl ester; lithium diisopropyl amide in tetrahydrofuran T=-70°C; 1 h; thermal stability, other temperature: 20 degC; Product distribution;

1: 69 percent / butyl-lithium / -78 - 25 °C 2: 99 percent / hydrogen / 10percent Pd-C / ethanol / 18 h / 760 Torr View Scheme