1.1: 89 percent / aq. LiOH / tetrahydrofuran / 12 h / 20 °C 2.1: 92 percent / acetonitrile / 60 h / 85 °C 3.1: LiN(SiMe3)2; HMPA / tetrahydrofuran / 1 h / -40 °C 3.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -78 °C 3.3: 73 percent / methanol; diethyl ether / 0.5 h / 0 °C 4.1: n-Bu4NF / tetrahydrofuran / 3 h / 20 °C 5.1: 90 percent / aq. NaOH / tetrahydrofuran / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1732799', constants.ctx, '0')">carbon tetrabromide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '610776', constants.ctx, '0')">triphenylphosphine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=0&deg;C;&nbsp;0.666667&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 87 percent / Pb(OAc)4 / CH₂Cl₂ / 0.5 h / -40 &deg;C<br />2: 80 percent / NaBH₄ / methanol; CH₂Cl₂ / 0.75 h<br />3: 88 percent / PPh₃; CBr₄ / CH₂Cl₂ / 0.67 h / 0 &deg;C<br /> <br /> &nbsp;