1: 1,3-dicyclohexylcarbodiimide / CHCl3 / Ambient temperature 2: CHCl3 / Ambient temperature 3: 89 percent / borane-THF / tetrahydrofuran / 24 h / Ambient temperature 4: 88.9 percent / SnCl2, conc. HCl / aq. ethanol / 3 h / Heating 5: 62.6 percent / iodomonochloride / acetic acid / 3.5 h / Ambient temperature 6: 1.) NaNO2, HCl, 2.) NaN3 / 1.) water, 0-5 deg C, 1 h, 2.) 30 min View Scheme

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

1: CHCl3 / Ambient temperature 2: 89 percent / borane-THF / tetrahydrofuran / 24 h / Ambient temperature 3: 88.9 percent / SnCl2, conc. HCl / aq. ethanol / 3 h / Heating 4: 62.6 percent / iodomonochloride / acetic acid / 3.5 h / Ambient temperature 5: 1.) NaNO2, HCl, 2.) NaN3 / 1.) water, 0-5 deg C, 1 h, 2.) 30 min View Scheme

1: 62.6 percent / iodomonochloride / acetic acid / 3.5 h / Ambient temperature 2: 1.) NaNO2, HCl, 2.) NaN3 / 1.) water, 0-5 deg C, 1 h, 2.) 30 min 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

hydrogenchloride; sodium azide; sodium nitrite 1.) water, 0-5 deg C, 1 h, 2.) 30 min; Yield given. Multistep reaction;