1: 89 percent / 48percent HBr / 7 h / Heating 2: 1.) Mg; 2.) p-TsOH / 1.) Li2CuCl4 / 1.) 2 h, ether, room t.; 2.) methanol, water, 1 h, reflux View Scheme

1.1: 11.2 g / red phosphorus; bromine / 0 - 20 °C 2.1: NaOEt / ethanol / 0.12 h / Heating 2.2: ethanol / 1 h / Heating 3.1: KOH / ethanol / 4 h / Heating 4.1: 3 h / 190 °C View Scheme

acetyl chloride und Leiten des Reaktionsprodukts im Stickstoff-Strom ueber Glaswolle bei 500grad;

1: pyridine / 1 h / 0 °C 2: LiBr / acetone / 5 h / Heating 4: KOH / ethanol; H2O / 5 h / Heating 5: 76 percent / N2H4*H2O, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 125 deg C, 6 h; 195 deg C, 3 h View Scheme

1: 89 percent / 48percent HBr / 7 h / Heating 2: 1.) Mg; 2.) p-TsOH / 1.) Li2CuCl4 / 1.) 2 h, ether, room t.; 2.) methanol, water, 1 h, reflux 3: 89 percent / 48percent HBr / 3 h / Heating 4: 55 percent / potassium tert-butoxide / benzene; dimethylsulfoxide / 0.17 h / 60 - 70 °C View Scheme

1.1: 11.2 g / red phosphorus; bromine / 0 - 20 °C 2.1: NaOEt / ethanol / 0.12 h / Heating 2.2: ethanol / 1 h / Heating 3.1: KOH / ethanol / 4 h / Heating 4.1: 3 h / 190 °C 5.1: 2.00 g / LiAlH4 / diethyl ether / 20 °C 6.1: red phosphorus; bromine / 0 - 20 °C 7.1: NaOEt / ethanol / 0.12 h / Heating 7.2: ethanol / 1 h / Heating 8.1: KOH / ethanol / 4 h / Heating 9.1: 1.1 g / 3 h / 190 °C View Scheme

1: pyridine / 0 °C 2: sodium bromide / dimethyl sulfoxide / 120 h 3: n-butyllithium / 1.) THF, hexane, -15 deg C, 18h, 2.) 6 deg C, 2d 4: mercury dichloride; mercury(II) oxide / methanol; water / 3 h / Heating View Scheme