1: 91 percent / Cu / dimethylformamide / 1 h / Heating 2: 50 percent / HSiCl3, NBu3 / xylene / 3 h / 130 °C View Scheme

1: 91 percent / Cu / dimethylformamide / 1 h / Heating 2: 50 percent / HSiCl3, NBu3 / xylene / 3 h / 130 °C View Scheme

boron tribromide in dichloromethane T=20°C; 12 h;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: H₂O₂ / methanol / 0.5 h / 20 &deg;C<br />2.1: LDA / tetrahydrofuran / 1.5 h / -78 &deg;C<br />2.2: 76 percent / I₂ / tetrahydrofuran / 1 h / -78 - 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: n-BuLi / tetrahydrofuran / 1 h / -78 &deg;C<br />1.2: tetrahydrofuran / 2 h / -78 - 20 &deg;C<br />2.1: H₂O₂ / methanol / 0.5 h / 20 &deg;C<br />3.1: LDA / tetrahydrofuran / 1.5 h / -78 &deg;C<br />3.2: 76 percent / I₂ / tetrahydrofuran / 1 h / -78 - 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: n-BuLi / tetrahydrofuran / 1 h / -78 &deg;C<br />1.2: tetrahydrofuran / 2 h / -78 - 20 &deg;C<br />2.1: H₂O₂ / methanol / 0.5 h / 20 &deg;C<br />3.1: LDA / tetrahydrofuran / 1.5 h / -78 &deg;C<br />3.2: 76 percent / I₂ / tetrahydrofuran / 1 h / -78 - 20 &deg;C<br /> <br /> &nbsp;