1H-imidazole; carbon tetrabromide; triphenylphosphine in tetrahydrofuran T=20°C; 3.5 h;

1: BH3*THF / tetrahydrofuran / 0 - 20 °C 2: 45 percent / Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; K2CO3 / dimethylformamide / 90 °C / 775.72 Torr 3: 74 percent / Ph3P; imidazole; CBr4 / tetrahydrofuran / 3.5 h / 20 °C View Scheme

1: 71 percent / Me4N(1+)*Cl(1-); POCl3 / 29 h / 140 - 150 °C 2: 96 percent / NaOMe / 48 h / Heating 3: BH3*THF / tetrahydrofuran / 0 - 20 °C 4: 45 percent / Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; K2CO3 / dimethylformamide / 90 °C / 775.72 Torr 5: 74 percent / Ph3P; imidazole; CBr4 / tetrahydrofuran / 3.5 h / 20 °C View Scheme

1: 96 percent / NaOMe / 48 h / Heating 2: BH3*THF / tetrahydrofuran / 0 - 20 °C 3: 45 percent / Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; K2CO3 / dimethylformamide / 90 °C / 775.72 Torr 4: 74 percent / Ph3P; imidazole; CBr4 / tetrahydrofuran / 3.5 h / 20 °C View Scheme

1: 45 percent / Pd(OAc)2; 1,3-bis(diphenylphosphino)propane; K2CO3 / dimethylformamide / 90 °C / 775.72 Torr 2: 74 percent / Ph3P; imidazole; CBr4 / tetrahydrofuran / 3.5 h / 20 °C View Scheme