1: caesium carbonate / acetonitrile / 20 °C 2: isopropylmagnesium chloride lithium chloride complex / tetrahydrofuran / 1 h / -78 °C 3: acetyl chloride / ethanol / 1.17 h / 20 - 50 °C View Scheme

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '471281', constants.ctx, '0')"><i>p</i>-toluidine</a> <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, '4153970', constants.ctx, '0')">sodium hydrogencarbonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />&nbsp;Cooling;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '1911173', constants.ctx, '0')">di-<i>tert</i>-butyl dicarbonate</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3629917', constants.ctx, '0')">sodium hexamethyldisilazane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br /> <br /> &nbsp;