1: pyridine / 12 h / 230 °C 2: 9.4 percent / ethanol; H2O / 31 h / 80 °C View Scheme

1.1: PPh3 / CH2Cl2 / 0.33 h / -20 °C 1.2: 95 percent / Et3N / CH2Cl2 / -70 - 20 °C 2.1: LDA / tetrahydrofuran; heptane / 0.5 h / -40 °C 2.2: 92 percent / tetrahydrofuran; heptane / 12 h / -70 - 20 °C View Scheme

1: bis (triortho-tolylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 2 h / 70 °C / |Inert atmosphere 2: diethyl chlorophosphate; lithium hexamethyldisilazane / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere View Scheme

1: diethyl chlorophosphate; lithium hexamethyldisilazane / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 2: bis (triortho-tolylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 70 °C / |Inert atmosphere View Scheme

1: pyridine / 12 h / 230 °C 2: 91 percent / ethanol; H2O / 31 h / 80 °C View Scheme

in dimethyl sulfoxide T=190°C; 6 h;

tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; zinc in N,N-dimethyl acetamide T=80°C; 3 h; Inert atmosphere;

in pyridine T=230°C; 12 h;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1912109', constants.ctx, '0')">9,10-Dibromoanthracene</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-90&deg;C;&nbsp;0.5&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">DMFA</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-90 - 20&deg;C;&nbsp;<br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1912109', constants.ctx, '0')">9,10-Dibromoanthracene</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-72&deg;C;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '110293', constants.ctx, '0')">(4-morpholinyl)methanone</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-72 - -35&deg;C;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;