1: With pyridinium tribromide; acetic acid in water T=20 - 50°C; 19 h; 2: With sodium hydroxide in water

hydrogen; palladium on activated charcoal in ethanol P=2585.7 Torr; 5 h; Ambient temperature;

ammonium formate; palladium 10 on activated carbon in isopropyl alcohol T=20 - 80°C; 2 h; Product distribution / selectivity;

1: 100 percent / BH3 / tetrahydrofuran 2: 100 percent / SOCl2, pyridine 3: 99 percent / ethanol; H2O 4: 97 percent / H2SO4, HOAc / H2O 5: SOCl2 6: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 7: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 8: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 9: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 10: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme

1: 100 percent / SOCl2, pyridine 2: 99 percent / ethanol; H2O 3: 97 percent / H2SO4, HOAc / H2O 4: SOCl2 5: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 6: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 7: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 8: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 9: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme

1: SOCl2 2: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 3: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 4: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 5: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 6: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme

1: 97 percent / H2SO4, HOAc / H2O 2: SOCl2 3: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 4: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 5: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 6: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 7: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme

1: K2CO3 / acetone; dimethylformamide; H2O / 18 h / Heating 2: HOAc, H2 / 10percent Pd/C / 20 h / 50 °C / 2585.7 Torr View Scheme

1: 99 percent / ethanol; H2O 2: 97 percent / H2SO4, HOAc / H2O 3: SOCl2 4: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 5: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 6: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 7: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 8: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme

1: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 2: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 3: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 4: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 5: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme