1: 1-bromo-3,5-difluoro-benzene With magnesium in tetrahydrofuran 1 h; Inert atmosphereReflux; 2: n-bromopentane With dilithium tetrachlorocuprate in tetrahydrofuran 48 h; RefluxInert atmosphere;

hydrogen; palladium on activated charcoal in pentane 4 h; Ambient temperature;

1: 69 percent / 1.) magnesium, 2.) ammonium chloride / diethyl ether; tetrahydrofuran; H2O / 2 h / Heating 2: phosphorus(V) oxide / pentane / Ambient temperature 3: 73 percent / H2 / 5percent palladium-on-charcoal / pentane / 4 h / Ambient temperature View Scheme

1: 69 percent / 1.) magnesium, 2.) ammonium chloride / diethyl ether; tetrahydrofuran; H2O / 2 h / Heating 2: phosphorus(V) oxide / pentane / Ambient temperature 3: 73 percent / H2 / 5percent palladium-on-charcoal / pentane / 4 h / Ambient temperature View Scheme

1: phosphorus(V) oxide / pentane / Ambient temperature 2: 73 percent / H2 / 5percent palladium-on-charcoal / pentane / 4 h / Ambient temperature View Scheme