1: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 2: 16 percent / NH3 / tetrahydrofuran / 3 h 3: 65 percent / 1 M NH4OH / 1 h / 70 °C 4: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature View Scheme

1: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 2: 16 percent / NH3 / tetrahydrofuran / 3 h 3: 65 percent / 1 M NH4OH / 1 h / 70 °C 4: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 5: 54 percent / 6 M HCl / 2 h / Heating View Scheme

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