1: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 2: 95 percent / acetonitrile / 15 h / 85 °C 3: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 4: 70 percent / Bu4NF / tetrahydrofuran 5: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT 6: 92 percent / acetonitrile / 15 h / 85 °C 7: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 8: 92 percent / LiOH / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 2: 95 percent / acetonitrile / 15 h / 85 °C 3: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 4: 70 percent / Bu4NF / tetrahydrofuran 5: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT 6: 92 percent / acetonitrile / 15 h / 85 °C 7: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT View Scheme

1: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 2: 95 percent / acetonitrile / 15 h / 85 °C 3: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 4: 70 percent / Bu4NF / tetrahydrofuran 5: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT View Scheme

1: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 2: 95 percent / acetonitrile / 15 h / 85 °C 3: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 4: 70 percent / Bu4NF / tetrahydrofuran View Scheme