1: 36 percent / DAST / neat (no solvent) / 0 deg C, 2 h; 25 deg C, 2 h 2: 73 percent / NBS View Scheme

1: neat (no solvent) 2: 36 percent / DAST / neat (no solvent) / 0 deg C, 2 h; 25 deg C, 2 h 3: 73 percent / NBS View Scheme

2,2'-azo-bisisobutyronitrile in tetrachloromethane 3 h; Inert atmosphereSchlenk techniqueReflux; Overall yield = 53 percent; Overall yield = 220.2 mg;

1: With 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane in chloroform Sommelet reaction; Heating; 2: With acetic acid

1: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C 2: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr View Scheme

1: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C 2: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr 3: 1.29 g / NaHCO3 / H2O; dioxane / 3 h / Ambient temperature 4: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH2Cl2 / -20 - 20 °C View Scheme

1: 89 percent / NaN3 / H2O; dimethylformamide / 2 h / Ambient temperature 2: 61 percent / PPh3 / diethyl ether; H2O / 12 h / Ambient temperature View Scheme