1: With hydrogen bromide; acetic acid 0.5 h; Reflux; 2: With sodium hydroxide T=20°C; pH=8;

hydrogen bromide in acetic acid T=100°C; 3 h;

1: 48 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 20 h / Ambient temperature 2: 100 percent / H2 / Pd/C 3: 67 percent / polyphosphoric acid / CHCl3 / 40 °C 4: 100 percent / K2CO3 / dimethylformamide / Heating 5: 42 percent / NH3(liq.), t-C4H9OK, air / Irradiation 6: 96 percent / 30percent Pd/C / 4 h / 250 °C 7: 90 percent / 48percent HBr / acetic acid / 3 h / 100 °C View Scheme

1: 93 percent / polyphosphoric acid / 4 h / 40 °C 2: 3 percent / HBr 3: 100 percent / K2CO3 / dimethylformamide / Heating 4: 42 percent / NH3(liq.), t-C4H9OK, air / Irradiation 5: 96 percent / 30percent Pd/C / 4 h / 250 °C 6: 90 percent / 48percent HBr / acetic acid / 3 h / 100 °C View Scheme

1: 67 percent / polyphosphoric acid / CHCl3 / 40 °C 2: 100 percent / K2CO3 / dimethylformamide / Heating 3: 42 percent / NH3(liq.), t-C4H9OK, air / Irradiation 4: 96 percent / 30percent Pd/C / 4 h / 250 °C 5: 90 percent / 48percent HBr / acetic acid / 3 h / 100 °C View Scheme

1: 1.) Hg(OAc)2, NaCl, 2.) I2 / 2.) ethanol, reflux, 25 min 2: 95 percent / 4N HCl / methanol / 8 h / Heating 3: 42 percent / NH3(liq.), t-C4H9OK, air / Irradiation 4: 96 percent / 30percent Pd/C / 4 h / 250 °C 5: 90 percent / 48percent HBr / acetic acid / 3 h / 100 °C View Scheme

1: 100 percent / K2CO3 / dimethylformamide / Heating 2: 42 percent / NH3(liq.), t-C4H9OK, air / Irradiation 3: 96 percent / 30percent Pd/C / 4 h / 250 °C 4: 90 percent / 48percent HBr / acetic acid / 3 h / 100 °C View Scheme

1: 95 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 20 h / Ambient temperature 2: 95 percent / H2 / Pd/C 3: 93 percent / polyphosphoric acid / 4 h / 40 °C 4: 3 percent / HBr 5: 100 percent / K2CO3 / dimethylformamide / Heating 6: 42 percent / NH3(liq.), t-C4H9OK, air / Irradiation 7: 96 percent / 30percent Pd/C / 4 h / 250 °C 8: 90 percent / 48percent HBr / acetic acid / 3 h / 100 °C View Scheme

1: 3 percent / HBr 2: 100 percent / K2CO3 / dimethylformamide / Heating 3: 42 percent / NH3(liq.), t-C4H9OK, air / Irradiation 4: 96 percent / 30percent Pd/C / 4 h / 250 °C 5: 90 percent / 48percent HBr / acetic acid / 3 h / 100 °C View Scheme

1: 95 percent / H2 / Pd/C 2: 93 percent / polyphosphoric acid / 4 h / 40 °C 3: 3 percent / HBr 4: 100 percent / K2CO3 / dimethylformamide / Heating 5: 42 percent / NH3(liq.), t-C4H9OK, air / Irradiation 6: 96 percent / 30percent Pd/C / 4 h / 250 °C 7: 90 percent / 48percent HBr / acetic acid / 3 h / 100 °C View Scheme