1: 74 percent / NaOAc, Br2 / acetic acid / 1.) 80 deg C, 6 h, 2.) 23 deg C, 64 h 2: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 3: 74 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 4: 56 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h View Scheme

bromine; sodium acetate in acetic acid 1.) 80 deg C, 6 h, 2.) 23 deg C, 64 h;;

1: 74 percent / anhydrous sodium acetate, Br2 / acetic acid / 1.) 80 deg C, 6 h, 2.) 23 deg C, 64 h; 2: 1.) n-butyllithium / 1.) ether, hexane, -70 deg C, 10 min, 2.) -55 to -70 deg C; View Scheme

trichlorophosphate in N,N-dimethyl-formamide T=100°C; 14 h;

racemic 2-di-tert-butylphosphino-1,1'-binaphthyl; palladium (II) trifluoroacetate; zinc in N,N-dimethyl acetamide T=80°C; 3 h;

1: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; sodium carbonate / 1,4-dioxane; water / 36 h / Reflux 2: ethylenediamine / 1,4-dioxane; propan-1-ol; water / 24 h / Reflux View Scheme

1.1: 53 percent / aq. H2O2; AcOH; (CF3CO)2O / 0 - 80 °C 2.1: H2SO4; HNO3 / 0 - 80 °C 2.2: Raney Ni / ethyl acetate; methanol View Scheme

1: phenyl-trifluoro-silane With tetrabutyl ammonium fluoride; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in tert-butyl alcohol T=20°C; Hiyama cross-coupling reaction; 0.0833333 h; Inert atmosphereSealed vial; 2: 5-chloro-2-methoxypyridine in tert-butyl alcohol T=60°C; Hiyama cross-coupling reaction; Inert atmosphereSealed vial;

4,5-dimethyl-3-(2-phenoxyphenyl)-1-(2,4,6-trimethylbenzyl)imidazolium chloride; palladium diacetate; caesium carbonate in 1,4-dioxane T=90°C; Suzuki-Miyaura Coupling; 18 h; Inert atmosphere;