1: 51 percent / H2SO4 / trifluoroacetic acid; CH2Cl2 2: 85 percent / HCOOH View Scheme

(ethylenedinitrilo)tetraacetic acid disodium salt; iron(II) chloride; ascorbic acid powder T=37°C; 1 h; 0.1 M phosphate buffer ( pH = 6.6 ); product distribution determined by MS of O-trimethylsilyl derivatives; Product distribution;

1: 95 percent / trifluoroacetic acid, H2SO4 / 3 h / Heating 2: 69 percent / glacial acetic acid, bromine / 2 h / Ambient temperature 3: 85 percent / formic acid / 4 h / Heating 4: 1.) n-BuLi, 2.) hexachloroethane / 1.) Et2O, THF, -70 deg C, 10 min, 2.) Et2O, THF, -70 deg C, 5 min 5: 3.1 g / benzene / 3 h / 60 °C 6: aq. HCl / acetic acid / 100 °C 7: 90 percent / boron tribromide / CH2Cl2; hexane / 1.) -70 deg C, 1 h, 2.) RT, 2 h View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8135994', constants.ctx, '0')">diborane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />8&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 85 percent / CH₂Cl₂ / 18 h / Ambient temperature<br />2: 94 percent / B₂H₆ / tetrahydrofuran / 8 h / Heating<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '18823246', constants.ctx, '0')">cerium(III) chloride heptahydrate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635685', constants.ctx, '0')">glycerol</a> <br />T=20&deg;C;&nbsp;0.75&nbsp;h;&nbsp;&nbsp;regioselective reaction;&nbsp;<br /> &nbsp;