tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=90°C; Alkylation; 1.5 h;

1: 88 percent / xylene / 48 h / 75 °C 2: 55 percent / H2 / Raney Ni / ethanol / 4 h / 2068.59 Torr 3: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 4: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 5: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 6: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C View Scheme

1: 55 percent / H2 / Raney Ni / ethanol / 4 h / 2068.59 Torr 2: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 3: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 4: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 5: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C View Scheme

1: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 2: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 3: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 4: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C View Scheme

1: thionyl chloride / 4 h / Heating 2: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 3: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 4: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 5: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C View Scheme

1: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C 2: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 3: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 4: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C View Scheme

1: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C 2: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 3: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C View Scheme

1: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating 2: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C View Scheme

1: With ozone in methanol; dichloromethane T=-78°C; Oxidation; 2: With dimethylsulfide in methanol; dichloromethane Hydrolysis;