bromine; acetic acid T=20°C; 2 h;

water; silver fluoride; trifluoroacetic acid T=40°C; 6 h; Green chemistry;

bromine

copper(ll) bromide in chloroform; ethyl acetate 5 h; Reflux;

in ethanol; water T=20°C;

1.1: K2CO3 / dimethylformamide / 0.5 h / 20 °C 1.2: 66 percent / dimethylformamide / 20 °C 2.1: 88 percent / NaH / dimethylformamide / 2 h / 20 °C 3.1: 33 percent / POCl3 / 3 h / Heating 4.1: 63 percent / HCl; H2 / 10 percent Pd/C / methanol / 2 h / 760 Torr View Scheme

1.1: K2CO3 / dimethylformamide / 0.5 h / 20 °C 1.2: 25 percent / dimethylformamide / 2 h / 20 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: 77 percent / aq. NaOH / ethanol / 0.5 h / Heating 3.1: 70 percent / PCl5 / 3 h / Heating 4.1: 80 percent / HCl; H2 / 10 percent Pd/C / methanol / 2 h / 760 Torr View Scheme

1.1: K2CO3 / dimethylformamide / 0.5 h / 20 °C 1.2: 25 percent / dimethylformamide / 2 h / 20 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: 77 percent / aq. NaOH / ethanol / 0.5 h / Heating View Scheme

1.1: potassium carbonate / 0.75 h / 40 - 45 °C 1.2: 18 h / 20 °C 2.1: hydrogenchloride / tetrahydrofuran / 20 °C / Cooling with ice 3.1: palladium 10 on activated carbon; hydrogen / ethanol / 24 h / 20 °C 4.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / -78 °C 5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 1.5 h / 20 °C / Molecular sieve View Scheme

1.1: acetone / Reflux 1.2: Reflux 2.1: trichlorophosphate / chloroform / 0 - 5 °C 2.2: Cooling; Reflux View Scheme