Et3NBCl3 in dichloromethane T=0°C; 0.25 h;

1: 1.) BBr3 / 1.) CH2Cl2 2: 48 percent / KF / dimethylformamide / 75 °C 3: 1.) aq. Na2S2O4, 2.) conc. H2SO4 / 2.) 20 -> 60 deg C 4: 70 percent / NaN(TMS)2 / tetrahydrofuran / 20 °C 5: 65 percent / NaHCO3 / Pd(OAc)2 / various solvent(s) / 15 h / 95 °C 6: 36 percent / CH2Cl2 / 4 h / Irradiation View Scheme

1: 48 percent / KF / dimethylformamide / 75 °C 2: 1.) aq. Na2S2O4, 2.) conc. H2SO4 / 2.) 20 -> 60 deg C 3: 70 percent / NaN(TMS)2 / tetrahydrofuran / 20 °C 4: 65 percent / NaHCO3 / Pd(OAc)2 / various solvent(s) / 15 h / 95 °C 5: 36 percent / CH2Cl2 / 4 h / Irradiation View Scheme

1: 48 percent / KF / dimethylformamide / 75 °C 2: 1.) aq. Na2S2O4, 2.) conc. H2SO4 / 2.) 20 -> 60 deg C 3: 70 percent / NaN(TMS)2 / tetrahydrofuran / 20 °C 4: 65 percent / NaHCO3 / Pd(OAc)2 / various solvent(s) / 15 h / 95 °C 5: 36 percent / CH2Cl2 / 4 h / Irradiation View Scheme

1: 70 percent / NaN(TMS)2 / tetrahydrofuran / 20 °C 2: 65 percent / NaHCO3 / Pd(OAc)2 / various solvent(s) / 15 h / 95 °C 3: 36 percent / CH2Cl2 / 4 h / Irradiation View Scheme

1: 1.) aq. Na2S2O4, 2.) conc. H2SO4 / 2.) 20 -> 60 deg C 2: 70 percent / NaN(TMS)2 / tetrahydrofuran / 20 °C 3: 65 percent / NaHCO3 / Pd(OAc)2 / various solvent(s) / 15 h / 95 °C 4: 36 percent / CH2Cl2 / 4 h / Irradiation View Scheme

1: 65 percent / NaHCO3 / Pd(OAc)2 / various solvent(s) / 15 h / 95 °C 2: 36 percent / CH2Cl2 / 4 h / Irradiation View Scheme

in dichloromethane 4 h; Irradiation;

1: NaClO2, NH2SO3H 3: selective mono-demethylation 4: K2CO3 / dimethylformamide 5: aq. Na2S2O4 6: K2CO3 / acetone / 6 h / Heating 7: aq. KOH / ethanol / 10 h / 25 °C 8: PPE / CHCl3 / 36 h / 25 °C 9: aq. KOH / ethanol / 8 h / 25 °C 11: PCC / CH2Cl2 / 15 h / 25 °C 12: 82 percent / K2CO3 / methanol / 36 h / 25 °C 13: 95 percent / ceric ammonium nitrate / acetonitrile; H2O 14: 85 percent / Et3N*BCl3 / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: selective mono-demethylation 2: K2CO3 / dimethylformamide 3: aq. Na2S2O4 4: K2CO3 / acetone / 6 h / Heating 5: aq. KOH / ethanol / 10 h / 25 °C 6: PPE / CHCl3 / 36 h / 25 °C 7: aq. KOH / ethanol / 8 h / 25 °C 9: PCC / CH2Cl2 / 15 h / 25 °C 10: 82 percent / K2CO3 / methanol / 36 h / 25 °C 11: 95 percent / ceric ammonium nitrate / acetonitrile; H2O 12: 85 percent / Et3N*BCl3 / CH2Cl2 / 0.25 h / 0 °C View Scheme