triethylamine in dichloromethane T=20°C; 2 h;

triethylamine in ethanol; dichloromethane; water

potassium hydroxide in xylene Heating;

1: 94 percent / KH (22percent) / benzene / 2 h / Heating 2: 95 percent / HCl (2N) / tetrahydrofuran / 3 h / Ambient temperature 3: 1.) Pb(OAc)4; 2.) NaBH4 / 1.) benzene, 2 h, room temp.; 2.) methanol, THF, room temp. 4: 1.) NEt3; 2.) KCl (0.1N) / 1.) CHCl3, room temp., 6h; 40 deg C, 12 h; 2.) 1 h 5: 2.) AgOAc / 1.) methanol, 55 deg C, overnight; 2.) 90 percent aqueous methanol, 2 h 6: 98 percent / H2 / palladium black / ethanol / 72 h / 50 °C / 760 Torr View Scheme

sodium hydrogencarbonate in dimethyl sulfoxide

sodium iodide Finkelstein reaction;

1: 94 percent / KH (22percent) / benzene / 2 h / Heating 2: 95 percent / HCl (2N) / tetrahydrofuran / 3 h / Ambient temperature 3: 1.) Pb(OAc)4; 2.) NaBH4 / 1.) benzene, 2 h, room temp.; 2.) methanol, THF, room temp. 4: 1.) NEt3; 2.) KCl (0.1N) / 1.) CHCl3, room temp., 6h; 40 deg C, 12 h; 2.) 1 h 5: 2.) AgOAc / 1.) methanol, 55 deg C, overnight; 2.) 90 percent aqueous methanol, 2 h 6: 98 percent / H2 / palladium black / ethanol / 72 h / 50 °C / 760 Torr 7: 91 percent / pyridine / 2 h / 70 °C View Scheme

1: 1.) KOH / 1.) xylene, 1h, reflux; 2.) xylene, 5h, reflux 2: HCl/methanol / 1 h / Heating View Scheme

(i) K, benzene, (ii) /BRN= 1913366/, (iii) aq. HCl, MeOH; Multistep reaction;

sodium bromide