hydrogen; palladium on activated charcoal in methanol; acetone T=50°C; 1 h;

1: 4 N aq. NaOH / benzene; CH2Cl2; H2O / 1 h / Ambient temperature 2: 1.) sec-BuLi, TMEDA, 2.) I2 / 1.) hexane, THF, -78 deg C, 1 h, 2.) hexane, THF, -20 deg C, 10 min 3: 81 percent / K2CO3, CuCl / propan-2-ol / 1.5 h / Heating 4: 69 percent / K2CO3 / dimethylformamide / 3 h / 20 - 45 °C 5: 1.) POCl3, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h 6: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 7: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

1: 12 percent / CuCl, K2CO3 / 2-ethoxy-ethanol / 6 h / Heating 2: 59 percent / polyphosphoric acid (PPA) / 1 h / 115 °C 3: 66 percent / K2CO3 / propan-2-ol / 2 h / Heating 4: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 5: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

1: 66 percent / K2CO3 / propan-2-ol / 2 h / Heating 2: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 3: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

1: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 2: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

1: 1.) sec-BuLi, TMEDA, 2.) I2 / 1.) hexane, THF, -78 deg C, 1 h, 2.) hexane, THF, -20 deg C, 10 min 2: 81 percent / K2CO3, CuCl / propan-2-ol / 1.5 h / Heating 3: 69 percent / K2CO3 / dimethylformamide / 3 h / 20 - 45 °C 4: 1.) POCl3, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h 5: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 6: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

1: 81 percent / K2CO3, CuCl / propan-2-ol / 1.5 h / Heating 2: 69 percent / K2CO3 / dimethylformamide / 3 h / 20 - 45 °C 3: 1.) POCl3, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h 4: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 5: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

1: 59 percent / polyphosphoric acid (PPA) / 1 h / 115 °C 2: 66 percent / K2CO3 / propan-2-ol / 2 h / Heating 3: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 4: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

1: 69 percent / K2CO3 / dimethylformamide / 3 h / 20 - 45 °C 2: 1.) POCl3, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h 3: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 4: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

1: 1.) POCl3, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h 2: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 3: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme