1.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: t-BuLi / pentane; diethyl ether / 0.17 h / -78 °C 2.2: CuBr*SMe2 / pentane; diethyl ether / 0.25 h / -78 °C 2.3: 50 percent / BF3*Et2O / pentane; diethyl ether / 4 h / -78 °C 3.1: 89 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C 4.1: 65 percent / NH3; Na / tetrahydrofuran / 0.25 h / -78 °C View Scheme

1.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: t-BuLi / pentane; tetrahydrofuran / 0.17 h / -78 °C 2.2: 56 percent / pentane; tetrahydrofuran / 0.25 h / -78 °C 3.1: 84 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C View Scheme

1.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: t-BuLi / pentane; diethyl ether / 0.17 h / -78 °C 2.2: CuBr*SMe2 / pentane; diethyl ether / 0.25 h / -78 °C 2.3: 50 percent / BF3*Et2O / pentane; diethyl ether / 4 h / -78 °C 3.1: 89 percent / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C 4.1: 65 percent / NH3; Na / tetrahydrofuran / 0.25 h / -78 °C 5.1: 55 percent / Et3N / tetrahydrofuran / 3 h / 20 °C View Scheme

1.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: t-BuLi / pentane; tetrahydrofuran / 0.17 h / -78 °C 2.2: pentane; tetrahydrofuran / 0.25 h / -78 °C 3.1: 205 mg / Bu4NF / tetrahydrofuran / 0.17 h / 20 °C View Scheme

1.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: t-BuLi / pentane; tetrahydrofuran / 0.17 h / -78 °C 2.2: pentane; tetrahydrofuran / 0.25 h / -78 °C 2.3: Bu4NF / tetrahydrofuran / 0.17 h / 20 °C View Scheme