sodium tetrahydroborate; water in methanol T=0°C;

1: 99 percent / pyridine / 1.) 0 degC, 15 min 2.) room temperature, 12 h 2: 68 percent / AlCl3 / CS2 / 0.5 h / Ambient temperature 3: 95 percent / PCl5 / POCl3 / 2 h / 45 - 50 °C 4: 92 percent / NaNH2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 degC 2.) 50 degC, 2 h View Scheme

1: 68 percent / AlCl3 / CS2 / 0.5 h / Ambient temperature 2: 95 percent / PCl5 / POCl3 / 2 h / 45 - 50 °C 3: 92 percent / NaNH2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 degC 2.) 50 degC, 2 h View Scheme

1: 92 percent / NaNH2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 degC 2.) 50 degC, 2 h View Scheme

1: 95 percent / PCl5 / POCl3 / 2 h / 45 - 50 °C 2: 92 percent / NaNH2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 degC 2.) 50 degC, 2 h View Scheme

Yield given. Multistep reaction;

tetrabutyl ammonium fluoride in tetrahydrofuran

carbon tetrabromide; triphenylphosphine in diethyl ether 4 h;

pyridine; phosphorus pentachloride in dichloromethane 2 h;