1: 80 percent / pyridine / 48 h / Ambient temperature 2: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 3: 50percent aq. MeOH / 4 h / Heating 4: HBr / dioxane / 20 h 5: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3903057', constants.ctx, '0')">boron trichloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />&nbsp;a) -78 deg C, 3 h, b) RT, overnight;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 1.) NaNO₂, HCl, 2.) HCl, H₂O / 1.) water, 2.5 h, 2.) 1 h<br />2: 88 percent / MgO, H₂ / 10percent Pd/C / dioxane / 2585.7 Torr<br />3: 84 percent / H₂ / Raney Ni / acetic acid / 2585.7 Torr<br />4: 89 percent / NaNO₂, AcOH, Ac₂O / 2 h / Ambient temperature<br />5: 90 percent / Heating<br />6: 83 percent / BCl₃ / CH₂Cl₂ / a) -78 deg C, 3 h, b) RT, overnight<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 88 percent / MgO, H₂ / 10percent Pd/C / dioxane / 2585.7 Torr<br />2: 84 percent / H₂ / Raney Ni / acetic acid / 2585.7 Torr<br />3: 89 percent / NaNO₂, AcOH, Ac₂O / 2 h / Ambient temperature<br />4: 90 percent / Heating<br />5: 83 percent / BCl₃ / CH₂Cl₂ / a) -78 deg C, 3 h, b) RT, overnight<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 276 mg / SOCl₂ / CHCl₃; dimethylformamide / Heating<br />2: 88 percent / MgO, H₂ / 10percent Pd/C / dioxane / 2585.7 Torr<br />3: 84 percent / H₂ / Raney Ni / acetic acid / 2585.7 Torr<br />4: 89 percent / NaNO₂, AcOH, Ac₂O / 2 h / Ambient temperature<br />5: 90 percent / Heating<br />6: 83 percent / BCl₃ / CH₂Cl₂ / a) -78 deg C, 3 h, b) RT, overnight<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 89 percent / NaNO₂, AcOH, Ac₂O / 2 h / Ambient temperature<br />2: 90 percent / Heating<br />3: 83 percent / BCl₃ / CH₂Cl₂ / a) -78 deg C, 3 h, b) RT, overnight<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 90 percent / Heating<br />2: 83 percent / BCl₃ / CH₂Cl₂ / a) -78 deg C, 3 h, b) RT, overnight<br /> <br /> &nbsp;