1: With thionyl chloride in 1,2-dichloro-ethane T=0 - 20°C; 2 h; 2: With water in 1,2-dichloro-ethane 3: With sodium hydrogencarbonate in water T=0°C; pH=8;

borane in tetrahydrofuran T=100°C; 1 h;

1: 97 percent / NBS, 48percent aq. HBr / CCl4 / Heating 2: 50 percent / NaOMe / diethyl ether / 24 h / Ambient temperature 3: 98 percent / KOH / ethanol; H2O / 6 h / Heating 4: 40 percent / urea / xylene / Heating 5: 68 percent / BH3 / tetrahydrofuran / 1 h / 100 °C View Scheme

1: 50 percent / NaOMe / diethyl ether / 24 h / Ambient temperature 2: 98 percent / KOH / ethanol; H2O / 6 h / Heating 3: 40 percent / urea / xylene / Heating 4: 68 percent / BH3 / tetrahydrofuran / 1 h / 100 °C View Scheme

1: 40 percent / urea / xylene / Heating 2: 68 percent / BH3 / tetrahydrofuran / 1 h / 100 °C View Scheme

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 40 percent / urea / xylene / Heating 3: 68 percent / BH3 / tetrahydrofuran / 1 h / 100 °C View Scheme

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -10 °C 1.2: 4 h / -10 - 20 °C 2.1: dimethylsulfide borane complex; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 80 °C 2.2: 0 °C 2.3: pH 8 3.1: thionyl chloride / anhydrous dichloroethane / 2 h / 0 - 20 °C 3.2: 0 °C / pH 8 View Scheme

1.1: dimethylsulfide borane complex; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 80 °C 1.2: 0 °C 1.3: pH 8 2.1: thionyl chloride / anhydrous dichloroethane / 2 h / 0 - 20 °C 2.2: 0 °C / pH 8 View Scheme

triethylamine in dichloromethane T=0°C; 2 h;