sodium carbonate in ethanol; water T=80°C; Suzuki-Miyaura coupling; 4 h;

1.1: lithium diisopropyl amide / tetrahydrofuran / 1.25 h / -78 °C 1.2: 0.5 h / -78 °C 2.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 °C / |Inert atmosphere 3.1: N,N-dimethylamino-1,1,2,2-tetrafluoroethane; pyridine hydrogenfluoride / dichloromethane / 7 h / 20 - 80 °C / |Inert atmosphere 4.1: triphenylphosphine; potassium carbonate; palladium dichloride / tetrahydrofuran; water / 12 h / 85 °C 5.1: sodium hydroxide / water; methanol / 1.5 h / 20 °C 6.1: 4-(N,N-dimethlyamino)pyridine; pyridine / toluene / 12.5 h / |Reflux 7.1: potassium carbonate / methanol / 0.5 h / 20 °C View Scheme

1: 1,2-difluoro-4-bromobenzene With magnesium; lithium chloride in tetrahydrofuran T=20°C; 2 h; Inert atmosphere; 2: With iron (III) acetylacetonate in tetrahydrofuran T=0°C; 0.0833333 h; Inert atmosphere; 3: ethylene,methyl acetate in tetrahydrofuran T=0°C; 0.75 h; Inert atmosphere;

1.1: Mg 1.2: 76 percent / sulphur 2.1: 95 percent / EtONa / 36 h / Heating View Scheme

1: 1,2-difluoro-4-bromobenzene With lithium diisopropyl amide in tetrahydrofuran; hexane T=-70°C; 1.5 h; 2: trifluoromethanesulfonic acid cyclopent-3-enylmethyl ester in tetrahydrofuran; hexane T=-70°C;

hydrogenchloride; sodium hydroxide; hydrogen sulfide; magnesium in benzene

{Pd2dba2*CHCl3}; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl; sodium t-butanolate in toluene T=80 - 85°C; 2.5 h;

1: (nitration) 2: Fe, aq. NH4Cl / Heating 3: (i) aq. NaNO2, H2SO4, (ii) /BRN= 4652394/, CuSO4, aq. NH3, CHCl3 4: methanol / Heating 5: aq. H2SO4 / acetic acid / Heating View Scheme