1.1: 53 percent / Br2 / CHCl3; toluene / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 78 °C 2.2: tributyl borate / hexane; tetrahydrofuran / 1.5 h / -78 °C 3.1: 1.0 g / aq. Na2CO3 / Pd(PPh3)4 / hexane; tetrahydrofuran View Scheme

1.1: 53 percent / Br2 / CHCl3; toluene / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 78 °C 2.2: tributyl borate / hexane; tetrahydrofuran / 1.5 h / -78 °C 3.1: 1.0 g / aq. Na2CO3 / Pd(PPh3)4 / hexane; tetrahydrofuran 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: tributyl borate / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 113 mg / aq. Na2CO3 / Pd(PPh3)4 / tetrahydrofuran; hexane / 70 °C View Scheme