1.1: NaH / tetrahydrofuran / 0 - 20 °C 1.2: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 20 °C 2.1: 98 percent / bromine; acetic acid / CH2Cl2 / 1.5 h / 20 °C 3.1: 95 percent / lithium aluminum hydride / tetrahydrofuran / 0.75 h / 0 °C 4.1: 91 percent / Pd(PPh3)4 / toluene / 110 °C 5.1: triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 6.1: lithium bromide / dimethylformamide; tetrahydrofuran / 20 °C View Scheme

1: 98 percent / bromine; acetic acid / CH2Cl2 / 1.5 h / 20 °C 2: 95 percent / lithium aluminum hydride / tetrahydrofuran / 0.75 h / 0 °C 3: 91 percent / Pd(PPh3)4 / toluene / 110 °C 4: triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 5: lithium bromide / dimethylformamide; tetrahydrofuran / 20 °C View Scheme

1: 91 percent / Pd(PPh3)4 / toluene / 110 °C 2: triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 3: lithium bromide / dimethylformamide; tetrahydrofuran / 20 °C View Scheme

1: 95 percent / lithium aluminum hydride / tetrahydrofuran / 0.75 h / 0 °C 2: 91 percent / Pd(PPh3)4 / toluene / 110 °C 3: triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 4: lithium bromide / dimethylformamide; tetrahydrofuran / 20 °C View Scheme

lithium bromide in tetrahydrofuran; N,N-dimethyl-formamide

1: triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 2: lithium bromide / dimethylformamide; tetrahydrofuran / 20 °C View Scheme