tetra-(n-butyl)ammonium iodide; potassium carbonate in acetone 1 h; Heating;

1: 88 percent / BCl3 / CH2Cl2 / 0.25 h / 0 °C 2: 6.4 g / K2CO3 / acetone / Heating; overnight View Scheme

potassium carbonate in acetone Heatingovernight;

hydrogenchloride; sodium methylate; thallium(III) nitrate 1.) methylene chloride, room temperature, 1 h; 2.) methanol, H2O, overnight; Yield given. Multistep reaction;

1: 1.) sulfur / 1.) 80 deg C, 1 h, 2.) reflux, 4 h 2: 93 percent / KOH / aq. ethanol / 9 h / Heating 3: 97 percent / HCl / 20 h / Ambient temperature 4: 97 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 5: 88 percent / N-bromosuccinimide/triphenylphosphine / benzene / 2 h / Ambient temperature View Scheme

1: 62 percent / sulfur / 80 degC, 1 h then reflux, 4 h 2: 93 percent / 50percent KOH, HCl / H2O; ethanol / 9 h / Heating 3: 97 percent / 10percent HCl / 20 h / Ambient temperature 4: 97 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 5: 88 percent / triphenylphosphine, N-bromosuccinimide / benzene / 2 h / Ambient temperature 6: 94 percent / benzene / 72 h / Heating 7: potassium ferricyanide, KOH 8: 82 percent / Raney nickel / aq. ethanol / 6 h / Heating View Scheme

1: 1.) sulfur / 1.) 80 deg C, 1 h, 2.) reflux, 4 h 2: 93 percent / KOH / aq. ethanol / 9 h / Heating 3: 97 percent / HCl / 20 h / Ambient temperature 4: 97 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature View Scheme

1: 1.) sulfur / 1.) 80 deg C, 1 h, 2.) reflux, 4 h 2: 93 percent / KOH / aq. ethanol / 9 h / Heating 3: 97 percent / HCl / 20 h / Ambient temperature View Scheme

1: 1.) Tl(NO3)3 on Montmorillinite clay; 2.) sodium methoxide; aq. HCl / 1.) methylene chloride, room temperature, 1 h; 2.) methanol, H2O, overnight 2: 94 percent / xylene / 18 h / Heating 3: POCl3 / toluene / 2 h / Heating 4: sodium acetate / Ambient temperature; overnight 5: 76 percent / H2 / 5percent Pd/CaCO3 / tetrahydrofuran / 6 h / Ambient temperature View Scheme