1: 89 percent / borane-THF / tetrahydrofuran / 24 h / Ambient temperature 2: 88.9 percent / SnCl2, conc. HCl / aq. ethanol / 3 h / Heating View Scheme

1: 89 percent / borane-THF / tetrahydrofuran / 24 h / Ambient temperature 2: 88.9 percent / SnCl2, conc. HCl / aq. ethanol / 3 h / Heating 3: 62.6 percent / iodomonochloride / acetic acid / 3.5 h / Ambient temperature View Scheme

1: 89 percent / borane-THF / tetrahydrofuran / 24 h / Ambient temperature 2: 88.9 percent / SnCl2, conc. HCl / aq. ethanol / 3 h / Heating 3: 62.6 percent / iodomonochloride / acetic acid / 3.5 h / Ambient temperature 4: 1.) NaNO2, HCl, 2.) NaN3 / 1.) water, 0-5 deg C, 1 h, 2.) 30 min View Scheme