1: 87.5 percent / Br2, (Ph)3P / acetonitrile / Ambient temperature 2: 88 percent / tetrahydrofuran 3: 1.) n-butyllithium / 1.) THF, -78 deg C, 4 h, 2.) THF, overnight 4: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 88 percent / tetrahydrofuran 2: 1.) n-butyllithium / 1.) THF, -78 deg C, 4 h, 2.) THF, overnight 3: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

2: 88 percent / diethyl ether / 1 h / Ambient temperature 3: 88 percent / I2 / benzene / 1 h / Heating 4: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 88 percent / diethyl ether / 1 h / Ambient temperature 2: 88 percent / I2 / benzene / 1 h / Heating 3: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 88 percent / I2 / benzene / 1 h / Heating 2: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 1.) n-butyllithium / 1.) THF, -78 deg C, 4 h, 2.) THF, overnight 2: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 58.5 percent / anhydrous potassium carbonate / butan-2-one / 192 h / Heating 2: potassium t-butoxide / toluene / 3 h / Heating 3: 84 percent / diethyl ether 4: 82 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 5 h / Heating 5: 82 percent / acetonitrile / 48 h / Ambient temperature 6: 1.) n-butyl-lithium, 3.) iodine 7: 94 percent / lithium aluminium hydride / diethyl ether / 12 h / Ambient temperature 8: 59 percent / oxalyl chloride, dimethyl sulphoxide / CH2Cl2 9: 5 percent / boron tri-iodide, ethylene / CH2Cl2 / -20 °C View Scheme

1: potassium t-butoxide / toluene / 3 h / Heating 2: 84 percent / diethyl ether 3: 82 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 5 h / Heating 4: 82 percent / acetonitrile / 48 h / Ambient temperature 5: 1.) n-butyl-lithium, 3.) iodine 6: 94 percent / lithium aluminium hydride / diethyl ether / 12 h / Ambient temperature 7: 59 percent / oxalyl chloride, dimethyl sulphoxide / CH2Cl2 8: 5 percent / boron tri-iodide, ethylene / CH2Cl2 / -20 °C View Scheme

1: 82 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 5 h / Heating 2: 82 percent / acetonitrile / 48 h / Ambient temperature 3: 1.) n-butyl-lithium, 3.) iodine 4: 94 percent / lithium aluminium hydride / diethyl ether / 12 h / Ambient temperature 5: 59 percent / oxalyl chloride, dimethyl sulphoxide / CH2Cl2 6: 5 percent / boron tri-iodide, ethylene / CH2Cl2 / -20 °C View Scheme

1: 41 percent / trifluoroacetic acid / 18 h / Heating 2: 58.5 percent / anhydrous potassium carbonate / butan-2-one / 192 h / Heating 3: potassium t-butoxide / toluene / 3 h / Heating 4: 84 percent / diethyl ether 5: 82 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 5 h / Heating 6: 82 percent / acetonitrile / 48 h / Ambient temperature 7: 1.) n-butyl-lithium, 3.) iodine 8: 94 percent / lithium aluminium hydride / diethyl ether / 12 h / Ambient temperature 9: 59 percent / oxalyl chloride, dimethyl sulphoxide / CH2Cl2 10: 5 percent / boron tri-iodide, ethylene / CH2Cl2 / -20 °C View Scheme