1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 3: SOCl2 / toluene / 1.25 h 4: AlCl3 / CS2 / 16 h / Ambient temperature 5: TiCl4 / toluene / 17 h / Ambient temperature 6: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 3: SOCl2 / toluene / 1.25 h 4: AlCl3 / CS2 / 16 h / Ambient temperature 5: TiCl4 / toluene / 17 h / Ambient temperature View Scheme

1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 3: SOCl2 / toluene / 1.25 h 4: AlCl3 / CS2 / 16 h / Ambient temperature 5: TiCl4 / toluene / 17 h / Ambient temperature 6: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 3: SOCl2 / toluene / 1.25 h 4: AlCl3 / CS2 / 16 h / Ambient temperature View Scheme

1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature View Scheme

Multi-step reaction with 7 steps 1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature3: SOCl2 / toluene / 1.25 h4: AlCl3 / CS2 / 16 h / Ambient temperature5: TiCl4 / toluene / 17 h / Ambient temperature6: sodium borohydride / methanol / 1.5 h / Ambient temperature  

Multi-step reaction with 7 steps 1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature3: SOCl2 / toluene / 1.25 h4: AlCl3 / CS2 / 16 h / Ambient temperature5: TiCl4 / toluene / 17 h / Ambient temperature6: sodium borohydride / methanol / 1.5 h / Ambient temperature