carbon tetrabromide; triphenylphosphine

1: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 2: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C 3: 83 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C View Scheme

1: 23 percent / K2CO3; 18-crown-6 / tetrahydrofuran / 12 h / Heating 2: (dimethylamino)pyridine; triethylamine / tetrahydrofuran / 3 h / 20 °C 3: lithium bromide / tetrahydrofuran / Heating View Scheme

1: 88 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C 2: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 3: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C 4: 83 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C View Scheme

1: 80 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 12 h / Heating 2: 98 percent / LiAlH4 / tetrahydrofuran / 6.5 h / 0 - 20 °C 3: 88 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C 4: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 5: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C 6: 83 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C View Scheme

1: 98 percent / LiAlH4 / tetrahydrofuran / 6.5 h / 0 - 20 °C 2: 88 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C 3: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 4: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C 5: 83 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C View Scheme

1: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C 2: 83 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 20 °C View Scheme

1: K2CO3; 18-crown-6 / acetone / Heating 2: LiAlH4 / tetrahydrofuran / 0 °C 3: CBr4; PPh3 / tetrahydrofuran 4: 97 percent / K2CO3; 18-crown-6 / acetone / Heating 5: LiAlH4 / tetrahydrofuran / 0 °C 6: CBr4; PPh3 / tetrahydrofuran View Scheme

lithium bromide in tetrahydrofuran Heating;

1: lithium bromide / tetrahydrofuran / Heating 2: 23 percent / K2CO3; 18-crown-6 / tetrahydrofuran / 12 h / Heating 3: (dimethylamino)pyridine; triethylamine / tetrahydrofuran / 3 h / 20 °C 4: lithium bromide / tetrahydrofuran / Heating View Scheme