hydrogen; palladium 10 on activated carbon in methanol 4 h;

1: chloroform / 4 h / 20 °C 2: hydrogen / palladium 10 on activated carbon / methanol / 4 h View Scheme

1: With hydrogenchloride; sodium nitrite T=-20°C; 0.25 h; 2: With tin(ll) chloride in water T=-20 - -5°C; 0.833333 h;

1.1: Br2 / methanol / 1 h / 20 °C 1.2: 26 percent / tetrahydrofuran / 0.5 h / 20 °C 2.1: 73 percent / LDA / cyclohexane; tetrahydrofuran / 20 h / Heating 3.1: 52 percent / Pd(OAc)2; Et3N; TBABr / dimethylformamide / 3 h / 80 °C 4.1: 71 percent / LiBH4 / tetrahydrofuran; toluene / 2 h / 100 °C View Scheme