1: bromine / methanol / 2 h / 0 °C 2: Pd2(PPh3)2Cl2; copper(l) iodide; triethylamine / 24 h / 20 °C 3: acetic acid / 4 h / 100 °C 4: tin(ll) chloride / ethyl acetate / 10 h / 20 °C 5: hydrogen / ethyl acetate / 5 h / 760.05 Torr 6: sodium cyanoborohydride / methanol / 1 h / 20 °C / pH Ca. 3 7: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / |Reflux 8: water / benzene / 120 °C 9: zinc; acetic acid / water / 5 h / 20 °C 10: boron trichloride / dichloromethane / -10 - 20 °C View Scheme

1: 73.6 percent / HCOOH, 30percent aq. H2O2 / 3.5 h / 0 - 5 °C 2: 95.5 percent / K2CO3 / dimethylformamide / 12.5 h / 60 - 70 °C 3: 96.6 percent / POCl3 / CH2Cl2 / 6 h / Ambient temperature 4: 92.7 percent / H2 / 5percent Pd/C / methanol / 760 Torr / Ambient temperature 5: 45.7 percent / AcONa / 120 h / Heating 6: 96.5 percent / H2SO4 / acetic acid / 2.5 h / Heating 7: 96.8 percent / K2CO3 / acetone / 7 h / Heating 8: 57.6 percent / CsF / various solvent(s) / 3 h / 190 - 195 °C / Heating 9: 1.) (CF3CO)2O, 30percent aq. H2O2, 2.) NaIO4, 3.) 1percent aq NaHCO3 View Scheme

1: sodium hydroxide / methanol / 12 h / 20 °C 2: triethylsilane; trifluoroacetic acid / 4 h / 20 °C 3: boron trichloride / dichloromethane / 0 °C View Scheme

1: 80 percent / ethanol; H2O / 6 h / Ambient temperature 2: 35 percent / CHCl3 / 0.5 h / Ambient temperature 3: 42 percent / P2O5 / 21 h / 60 - 70 °C 4: 80 percent / BH3 / tetrahydrofuran / 4 h / Heating 5: 100 percent / KOH / H2O; ethanol / 1 h / Heating 6: 55 percent / 5percent Pd/C / acetic acid / 24 h / Heating View Scheme

hydroxylamine hydrochloride

1: 98 percent / hydroxylamine hydrochloride 2: 98 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme

bromine in methanol T=0 - 20°C;