hydrogen bromide in propionic acid 6 h; Heating;

1: 71 percent / aq. hydrobromic acid / propionic acid / 6 h / Heating 2: 75 percent / aq. nitric acid / propionic acid / 1 h / 5 °C 3: 94 percent / hydrogen / 10 percent Pd/C / tetrahydrofuran / 2585.74 Torr View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1732991', constants.ctx, '0')">N,N,N',N,-tetramethylethylenediamine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '4948473', constants.ctx, '0')">magnesium</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11323458', constants.ctx, '0')">anhydrous iron chloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=20&deg;C;&nbsp;&nbsp;Product distribution / selectivity;&nbsp;<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11324891', constants.ctx, '0')">Fe(acac)3</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1732991', constants.ctx, '0')">N,N,N',N,-tetramethylethylenediamine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '2018', constants.ctx, '0')">1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;1.33333&nbsp;h;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11324644', constants.ctx, '0')">palladium diacetate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3556712', constants.ctx, '0')">potassium <i>tert</i>-butylate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '9932898', constants.ctx, '0')">1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102551', constants.ctx, '0')">1,4-dioxane</a> <br />T=20&deg;C;&nbsp;Suzuki coupling;&nbsp;26&nbsp;h;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11324644', constants.ctx, '0')">palladium diacetate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3556712', constants.ctx, '0')">potassium <i>tert</i>-butylate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '9932898', constants.ctx, '0')">1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102551', constants.ctx, '0')">1,4-dioxane</a> <br />T=90&deg;C;&nbsp;Suzuki coupling;&nbsp;30&nbsp;h;&nbsp;<br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1735227', constants.ctx, '0')">1-bromo-decane</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4948473', constants.ctx, '0')">magnesium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a> <br />T=20&deg;C;&nbsp;1.5&nbsp;h;&nbsp;&nbsp;Inert atmosphereReflux;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '1237590', constants.ctx, '0')">1-bromo-4-methoxy-benzene</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '15680983', constants.ctx, '0')">[1,3-bis(diphenylphosphino) propane] dichloronickel(II)</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a> <br />5&nbsp;h;&nbsp;&nbsp;Reflux;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: AlCl₃; 1,1,2,2-tetrachloro-ethane<br />2: N₂H₄+H₂O; KOH; diethylene glycol<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '14338702', constants.ctx, '0')">[1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: BF₃ <br />2: H₂ / Pd-C / acetic acid<br /> <br /> &nbsp;