sodium carbonate; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran T=80°C; Substitution; 2 h;

1: 67 percent / dimethylcarbamyl chloride / toluene / 20 h / 60 °C 2: 74 percent / HBr / acetic acid / 1 h / 25 °C 3: 90 percent / bis(dibenzylideneacetone)palladium; triphenylphosphine; aq. K2CO3 / toluene; dimethylformamide / 4 h / Heating 4: 60 percent / sodium nitrite / dimethylformamide / 3 h / 25 °C 5: 94 percent / bis(dibenzylideneacetone)palladium; triphenylphosphine; 2 N aq. Na2CO3 / tetrahydrofuran / 2 h / 80 °C View Scheme

1: 90 percent / bis(dibenzylideneacetone)palladium; triphenylphosphine; aq. K2CO3 / toluene; dimethylformamide / 4 h / Heating 2: 60 percent / sodium nitrite / dimethylformamide / 3 h / 25 °C 3: 94 percent / bis(dibenzylideneacetone)palladium; triphenylphosphine; 2 N aq. Na2CO3 / tetrahydrofuran / 2 h / 80 °C View Scheme

1: 74 percent / HBr / acetic acid / 1 h / 25 °C 2: 90 percent / bis(dibenzylideneacetone)palladium; triphenylphosphine; aq. K2CO3 / toluene; dimethylformamide / 4 h / Heating 3: 60 percent / sodium nitrite / dimethylformamide / 3 h / 25 °C 4: 94 percent / bis(dibenzylideneacetone)palladium; triphenylphosphine; 2 N aq. Na2CO3 / tetrahydrofuran / 2 h / 80 °C View Scheme