sodium sulfide in 1,4-dioxane 20 h; Heating;

Lawesson's reagent in chlorobenzene 1 h; Heating;

1: 96 percent / triphenylphosphine / CH2Cl2 / 1.) 0 deg C, 2.) room temp., 1 h 2: 95.9 percent / n-BuLi / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) room temp., 1 h 3: 98.5 percent / Cu2Cl2, N,N,N',N'-tetramethylethylenediamine / 1,2-dimethoxy-ethane / 2 h / 30 - 35 °C 4: 97.5 percent / Na2S*9H2O / dioxane / 20 h / Heating View Scheme

1: 98.5 percent / Cu2Cl2, N,N,N',N'-tetramethylethylenediamine / 1,2-dimethoxy-ethane / 2 h / 30 - 35 °C 2: 97.5 percent / Na2S*9H2O / dioxane / 20 h / Heating View Scheme

1: 95.9 percent / n-BuLi / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) room temp., 1 h 2: 98.5 percent / Cu2Cl2, N,N,N',N'-tetramethylethylenediamine / 1,2-dimethoxy-ethane / 2 h / 30 - 35 °C 3: 97.5 percent / Na2S*9H2O / dioxane / 20 h / Heating View Scheme

1: thien-2-yl bromide With magnesium in diethyl ether 2 h; Heating; 2: 2,5-dibromothiophene With [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in diethyl ether; benzene 6 h; Heating;

copper T=210°C;