thionyl chloride; tin(IV) chloride in dichloromethane T=20°C; 1 h;

1: With hydrogen bromide; acetic acid in dichloromethane T=0°C; 2: With sodium acetate; copper; acetic acid; zinc in tetrahydrofuran

hydrogen bromide in dichloromethane; acetic acid T=0 - 20°C; 3 h;

1.1: 32percent HBr / 1,2-dichloro-ethane; acetic acid / 2 h / 0 °C 1.2: 6.22 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dichloro-ethane / 0.5 h / 20 °C 2.1: SnCl4 / CH2Cl2 / -18 °C 3.1: 88 percent / CeCl3*7H2O; NaBH4 / methanol / 0.33 h / 0 °C 4.1: 82 percent / OsO4; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H2O / 16 h / 20 °C View Scheme

1.1: morpholine / dichloromethane / 20 °C / Inert atmosphere 2.1: dichloromethane / 1 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: boron trifluoride dimethyl etherate / dichloromethane / 20 °C / Inert atmosphere 4.1: methanol; sodium methylate / 0.5 h / 20 °C View Scheme

1.1: 93 percent / HBr; AcOH / CH2Cl2 / 4 h / 0 - 25 °C 2.1: 82 percent / 2,6-lutidine / nitromethane / 12 h / 25 °C 3.1: NaOMe / methanol / 3 h / 25 °C 4.1: NaH / tetrahydrofuran / 0 °C 4.2: 5.14 g / tetrabutylammonium chloride / tetrahydrofuran / 4 h / Heating 5.1: ZnCl2 / CH2Cl2 / -60 - 0 °C 6.1: 3.4 g / NaOMe / methanol / 4 h / 25 °C 7.1: 97 percent / DMAP; Et3N / CH2Cl2 / 48 h / 25 °C 8.1: 88 percent / NBS; H2O / CH2Cl2 / 1 h / 25 °C 9.1: 555 mg / DBU / CH2Cl2 / 12 h / 25 °C 10.1: 93 percent / BF3*Et2O; 4 Angstroem molecular sieves / CH2Cl2 / -78 - -20 °C 11.1: NBS; H2O / CH2Cl2 / 2 h / 25 °C 11.2: 98 percent / DBU / CH2Cl2 / 12 h / 25 °C 12.1: 71 percent / TMSOTf; 4 Angstroem molecular sieves / CH2Cl2 / 5 h / -20 °C 13.1: DDQ; H2O / CH2Cl2 / 12 h / 25 °C 13.2: 81 percent / Pd(CN)2Cl2; H2O / acetone / 2 h / 25 °C View Scheme

1: hydrogen bromide; acetic acid / dichloromethane / 3 h / 0 °C 2: CuSO4‵5H2O; acetic acid; zinc / water / 2.5 h / 0 °C 3: methanol; sodium methylate / 4 h / 20 °C 4: dipyridinium dichromate; acetic acid / ethyl acetate / 16 h / 20 °C 5: caesium carbonate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 6: Oxonereg;; C8H6O4(2-)*Cu(2+) / toluene / 6 h / 60 °C / Molecular sieve; Air atmosphere 7: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane 8: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme

1: hydrogen bromide; acetic acid / dichloromethane / 3 h / 0 °C 2: CuSO4‵5H2O; acetic acid; zinc / water / 2.5 h / 0 °C 3: methanol; sodium methylate / 4 h / 20 °C 4: dipyridinium dichromate; acetic acid / ethyl acetate / 16 h / 20 °C 5: Oxonereg;; C8H6O4(2-)*Cu(2+) / toluene / 7 h / 60 °C / Molecular sieve; Air atmosphere 6: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / Reflux View Scheme

trimethylsilylazide; tin(IV) chloride in dichloromethane