1: 84 percent / HCl / diethyl ether / 48 h / Heating 2: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 3: 64 percent / aq. HCl / tetrahydrofuran / 0.5 h / 40 °C 5: 24 percent / electrochemical oxidation View Scheme

1: 84 percent / HCl / diethyl ether / 48 h / Heating 2: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h 3: 54 percent / Ac2O / 48 h / Ambient temperature 4: 82 percent / aq. NaOH / CH2Cl2; methanol / 1 h / Ambient temperature 5: 1.) NaH / 1.) THF, room temperature - 30 min, reflux - 15 min, 2.) THF, room temperature, 20 h 6: 100 percent / aq. NaOH / 24 h / Heating 7: ceric ammonium sulfate 8: NH3 View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587194', constants.ctx, '0')">iodine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '505950', constants.ctx, '0')">2-methyl-2-iodopropane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8135986', constants.ctx, '0')">iron(II) chloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '506008', constants.ctx, '0')">dimethyl sulfoxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '742035', constants.ctx, '0')">trifluoroacetic acid</a> <br />T=80&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 55 percent / NBS / dimethylformamide / 3.08 h / 60 &deg;C<br />2: 76 percent / TFA, t-BuI, I₂, FeCl₂ / dimethylsulfoxide / 5 h / 80 - 85 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 63 percent / HNO₃ / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min<br />2: 55 percent / NBS / dimethylformamide / 3.08 h / 60 &deg;C<br />3: 76 percent / TFA, t-BuI, I₂, FeCl₂ / dimethylsulfoxide / 5 h / 80 - 85 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 1.) AcOH, FeCl₃, 2.) AcOH / 1.) 60 deg C, 5 min, 2.) reflux, 5 h<br />2: 63 percent / HNO₃ / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min<br />3: 55 percent / NBS / dimethylformamide / 3.08 h / 60 &deg;C<br />4: 76 percent / TFA, t-BuI, I₂, FeCl₂ / dimethylsulfoxide / 5 h / 80 - 85 &deg;C<br /> <br /> &nbsp;