1.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 6.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 6.2: 12.5 h / 0 - 5 °C 7.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 7.2: 0.5 h / 0 - 5 °C 8.1: hydrogenchloride / anhydrous dichloroethane; water / 0 - 5 °C / pH 2.5 8.2: 14.25 h / 0 - 30 °C 9.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 10.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 11.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C View Scheme

trimethylsilyl bromide T=20°C; 0.166667 h;

in hexane; chloroform

1: PBr3 / CH2Cl2 2: 76 percent / LiHMDS / tetrahydrofuran 3: 81 percent / LiOH; H2O2 4: 95 percent / LAH / tetrahydrofuran 5: 97 percent / PPh3; NBS / CH2Cl2 View Scheme

1: PBr3 / CH2Cl2 2: 76 percent / LiHMDS / tetrahydrofuran 3: 81 percent / LiOH; H2O2 4: 95 percent / LAH / tetrahydrofuran 5: 97 percent / PPh3; NBS / CH2Cl2 6: 68 percent / n-BuLi 7: HCl / acetonitrile 8: Et3N 9: NaBH4 / ethanol 10: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2 View Scheme

1: PBr3 / CH2Cl2 2: 76 percent / LiHMDS / tetrahydrofuran 3: 81 percent / LiOH; H2O2 4: 95 percent / LAH / tetrahydrofuran View Scheme

1: PBr3 / CH2Cl2 2: 76 percent / LiHMDS / tetrahydrofuran 3: 81 percent / LiOH; H2O2 4: 95 percent / LAH / tetrahydrofuran 5: 97 percent / PPh3; NBS / CH2Cl2 6: 68 percent / n-BuLi 7: HCl / acetonitrile 8: Et3N 9: NaBH4 / ethanol View Scheme

1: PBr3 / CH2Cl2 2: 76 percent / LiHMDS / tetrahydrofuran 3: 81 percent / LiOH; H2O2 4: 95 percent / LAH / tetrahydrofuran 5: 97 percent / PPh3; NBS / CH2Cl2 6: 68 percent / n-BuLi 7: HCl / acetonitrile 8: Et3N 9: NaBH4 / ethanol 10: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2 11: Mg 12: 23 percent / H2 / Pd(OH)2/C 13: 38 percent / TPAP; NMMO 14: 65 percent / 2-hydroxypyridine; Et3N View Scheme

1: PBr3 / CH2Cl2 2: 76 percent / LiHMDS / tetrahydrofuran 3: 81 percent / LiOH; H2O2 View Scheme

1: PBr3 / CH2Cl2 2: 76 percent / LiHMDS / tetrahydrofuran 3: 81 percent / LiOH; H2O2 4: 95 percent / LAH / tetrahydrofuran 5: 97 percent / PPh3; NBS / CH2Cl2 6: 68 percent / n-BuLi 7: HCl / acetonitrile 8: Et3N 9: NaBH4 / ethanol 10: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2 11: Mg 12: 23 percent / H2 / Pd(OH)2/C 13: 38 percent / TPAP; NMMO View Scheme