sulfur(IV) fluoride in hydrogen fluoride T=20°C; 12 h; steel autoclave;

1: 93 percent / 10percent aq. NaOH / 1.5 h / Heating 2: SOCl2 / 0.5 h / Heating 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 3 h 4: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h 5: 76 percent / tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C 6: 82 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C 7: 81 percent / H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr View Scheme