1: 95 percent / BBr3 / CH2Cl2 / Ambient temperature 2: 92 percent / pyridine / 18 h View Scheme

1: 95 percent / BBr3 / CH2Cl2 / Ambient temperature 2: 92 percent / pyridine / 18 h 3: 77 percent / (PhSeO)2O / tetrahydrofuran / 4 h / Heating View Scheme

boron tribromide in dichloromethane Ambient temperature;

1: (i), (ii) aq. HCl, NH4Cl 2: H2 / Adams catalyst View Scheme

palladium on activated charcoal in various solvent(s) 0.5 h; Heating;

palladium on activated charcoal in various solvent(s) 4 h; Heating;

1: 73 percent / H2 / 10percent Pd/C / ethyl acetate / 24 h / 2585.7 Torr / Ambient temperature 2: 83 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / acetic acid; H2O / 24 h / Ambient temperature 3: 90 percent / 10percent Pd/C / various solvent(s) / 0.5 h / Heating View Scheme

1: 83 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / acetic acid; H2O / 24 h / Ambient temperature 2: 90 percent / 10percent Pd/C / various solvent(s) / 0.5 h / Heating View Scheme

Yield given. Multistep reaction. Yields of byproduct given;

1: BBr3 / CH2Cl2 / 1.5 h / -78 °C 2: 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 3 h 3: 83 percent / NaBH4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 4: 81 percent / 4-(N,N-dimethylamino)pyridine, imidazole / CH2Cl2 / 2 h / Ambient temperature 5: 100 percent / 0.1 M KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature 6: 72 percent / (SO3K)2NO, KH2PO4, Adogen 464 / benzene 7: 96 percent / NaBH4, O2 / ethanol / 84 h 8: 54 percent / 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 1.5 h 9: 58 percent / n-Bu4NF / tetrahydrofuran / 4 h 10: 85 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / tetrahydrofuran / 5 h / Ambient temperature 11: 99 percent / NaOMe / tetrahydrofuran; methanol / 0.17 h / Heating View Scheme