hydrogenchloride; palladium monocarbide in ethanol; water; ethyl acetate

1: 65 percent / 10percent aq NaNO2 / aq. HCl / 0 °C 2: 80 percent / H2 / 10percent Pd-C / ethyl acetate / 60 °C / 760 Torr View Scheme

1: 80 percent / ethanol / 4 h / Heating 2: 65 percent / 10percent aq NaNO2 / aq. HCl / 0 °C 3: 80 percent / H2 / 10percent Pd-C / ethyl acetate / 60 °C / 760 Torr View Scheme

1: 71 percent / sodium ethoxide / ethanol / room temp. 4 h, reflux, 1 h 2: 96 percent / hydrogen / 5percent Pd/C / ethanol / Ambient temperature View Scheme

acetic acid 0.0833333 h; Heating;

1: iodine; sodium hydrogencarbonate / water / 30 h 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3: tert-butyl alcohol / 15 h / 60 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux 5: ethanol; toluene-4-sulfonic acid / 15 h 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 7: 5 h / 60 °C 8: hydrogenchloride / tetrahydrofuran; ethyl acetate / 0.5 h / 20 °C View Scheme

1: 91 percent / ICl, CaCO3 / methanol; H2O 2: 1.) 2 molpercent Pd(OAc)2, Na2CO3; 2.) HCl / 1.) DMF, 100 deg C; 2.) MeOH View Scheme

iodine; sodium hydrogencarbonate in water 30 h;

iodine cloride; calcium carbonate in methanol; water

1: With hydrogenchloride; sodium nitrite in water T=-5 - 0°C; 0.75 h; Saturated solution; 2: With sodium sulfite in water T=0 - 65°C; 17.25 h;