N-chloro-succinimide; silver nitrate in water; acetonitrile T=0°C; 0.75 h;

1: 96 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -10 deg C, 2 h, 2.) -10 deg C, 1 h; refrigerator, 18 h 2: 9 percent / p-TsOH / tetrahydrofuran / 16 h / 25 °C 3: 50 percent / AgNO3, NCS / acetonitrile; H2O / 0.75 h / 0 °C View Scheme

1: 72 percent / Li2CO3, LiBr / dimethylformamide / 3 h / 130 °C 2: 96 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -10 deg C, 2 h, 2.) -10 deg C, 1 h; refrigerator, 18 h 3: 9 percent / p-TsOH / tetrahydrofuran / 16 h / 25 °C 4: 50 percent / AgNO3, NCS / acetonitrile; H2O / 0.75 h / 0 °C View Scheme

1: 100 percent / NBS / CCl4 / 12 h / Heating 2: 72 percent / Li2CO3, LiBr / dimethylformamide / 3 h / 130 °C 3: 96 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -10 deg C, 2 h, 2.) -10 deg C, 1 h; refrigerator, 18 h 4: 9 percent / p-TsOH / tetrahydrofuran / 16 h / 25 °C 5: 50 percent / AgNO3, NCS / acetonitrile; H2O / 0.75 h / 0 °C View Scheme