triphenylphosphine; silver carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in dichloromethane; water T=60°C; 24 h;

2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=20°C; 11 h; Molecular sieve;

1: 1,3-oxazole With TMPZnCl*LiCl in tetrahydrofuran T=0°C; 1 h; Inert atmosphereSchlenk technique; 2: 1-chloro-4-iodobenzene With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran T=50°C; Negishi Coupling; 2 h; Inert atmosphereSchlenk technique; regioselective reaction;

1: 46 percent / Et3N / benzene / 24 h / Heating 2: 30 percent / NBS / AIBN / CCl4 / 12 h / Heating 3: 1.) BuLi, 2.) water / 1.) THF, -18 deg C, 15 min, 2.) room temp., overnight View Scheme

1: sodium acetate / 100 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 11 h / 20 °C / |Molecular sieve View Scheme

n-butyllithium; water 1.) THF, -18 deg C, 15 min, 2.) room temp., overnight; Yield given. Multistep reaction;

(i) HNO2, (ii) CuCl; Multistep reaction;

(i) , (ii) P2O5, H2SO4; Multistep reaction;