1: 1.) N-bromosuccinimide (NBS), AIBN, 2.) NaI / 1.) carbon tetrachloride, 12 h, reflux, 2.) acetone, 2 h, reflux 2: 92 percent / O3 / methanol / -78 - 20 °C View Scheme

1: sodium tetrahydridoborate / ethanol 2: 76 percent / N,N-dimethylaniline / diethyl ether / 2 h / Heating 3: 18 percent / acetyl nitrate / acetic anhydride / 2 h / -30 - -10 °C View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: CH₂Cl₂ / 1 h / -78 &deg;C / Irradiation<br />2: potassium carbonate / ethane-1,2-diol / 4 h / 120 &deg;C<br />3: 85 percent / aluminum chloride / CH₂Cl₂ / 1 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 51 percent / CH₂Cl₂ / 1 h / -78 &deg;C / Irradiation<br />2: potassium carbonate / ethane-1,2-diol / 4 h / 120 &deg;C<br />3: 85 percent / aluminum chloride / CH₂Cl₂ / 1 h / 0 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209238', constants.ctx, '0')">aluminium trichloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '507540', constants.ctx, '0')">nitrobenzene</a> <br />T=5&deg;C;&nbsp;6&nbsp;h;&nbsp;<br /> &nbsp;