1: 88 percent / acetic acid; hydrogen / Pd/C / ethanol / 2.5 h / 25 °C / 3102.89 Torr 2: 94 percent / sodium bicarbonate; potassium iodide / dimethylformamide / 50 - 68 °C 3: 93 percent / H2O; acetic acid / 105 °C View Scheme

1: BF3*OEt2 / CH2Cl2 / 20 °C 2: 60 percent / ceric ammonium nitrate; O2 / acetonitrile / 3 h / 20 °C 3: 56 percent / m-chloroperoxybenzoic acid; Na2CO3 4: 79 percent / H2 / Pd/C View Scheme

1: BF3*OEt2 / CH2Cl2 / 20 °C 2: 60 percent / ceric ammonium nitrate; O2 / acetonitrile / 3 h / 20 °C 3: 56 percent / m-chloroperoxybenzoic acid; Na2CO3 View Scheme

1.1: 88 percent / acetic acid; hydrogen / Pd/C / ethanol / 2.5 h / 25 °C / 3102.89 Torr 2.1: 94 percent / sodium bicarbonate; potassium iodide / dimethylformamide / 50 - 68 °C 3.1: 93 percent / H2O; acetic acid / 105 °C 4.1: NaH / tetrahydrofuran / 0.5 h / 25 °C 4.2: t-BuLi / tetrahydrofuran / 0.92 h / -72 °C 4.3: 60 percent / tetrahydrofuran / 2.5 h / -72 °C View Scheme

hydrogen; acetic acid; palladium on activated charcoal in ethanol T=25°C; Hydrogenolysis; P=3102.89 Torr; 2.5 h;

in tetrahydrofuran T=-20 - 20°C; Phenylation; 0.833333 h;

in tetrahydrofuran T=-78°C;

1: 99 percent / triethylamine / tetrahydrofuran; H2O / 2 h / 25 °C 2: 73 percent / tetrahydrofuran / 0.83 h / -20 - 20 °C View Scheme

1: 99 percent / triethylamine / tetrahydrofuran; H2O / 2 h / 25 °C 2: 73 percent / tetrahydrofuran / 0.83 h / -20 - 20 °C View Scheme

1: CH2Cl2 / 0 °C 2: tetrahydrofuran / -78 °C View Scheme