trimethylsilyl bromide T=20°C; 0.166667 h;

in hexane; chloroform

1: NaBH4 / ethanol 2: PBr3 / CH2Cl2 View Scheme

1: 98 percent / K2CO3 / acetonitrile 2: NaBH4 / ethanol 3: PBr3 / CH2Cl2 View Scheme

1: 72 percent / NaOMe / methanol / 1.5 h / Heating 2: 96 percent / NaBH4 / methanol / 1 h / 20 °C 3: 100 percent / Me3SiBr / 0.17 h / 20 °C View Scheme

1: potassium carbonate / acetonitrile / 10 h / 25 - 35 °C / Reflux 2: phosphorus tribromide / dichloromethane / 2 h / 0 - 10 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 5.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 5.2: 1 h / 0 - 5 °C View Scheme

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

1: 76 percent / LiHMDS / tetrahydrofuran 2: 81 percent / LiOH; H2O2 3: 95 percent / LAH / tetrahydrofuran 4: 97 percent / PPh3; NBS / CH2Cl2 5: 68 percent / n-BuLi View Scheme