potassium hydroxide

tetrachloromethane; iodine; chlorine

1: n-BuLi / 1.) ether, -78 deg C - -40 deg C; 2.) -40 deg C - 0 deg C 2: 69 percent / 2,4-Dinitrobenzenesulfenyl chloride, NEt3 / CH2Cl2 / 1 h / 25 °C 3: m-Chloroperbenzoic acid (85percent), NaHCO3 / CCl4; H2O / 1 h / 0 °C 4: 1.) NBS; 2.) 1,5-Diazabicyclo<5.4.0>undec-5-ene / 1.) CCl4, reflux, 1 h, sunlamp; 2.) CH2Cl2, 25 deg C, 0.5 h 5: pyridine / 0.17 h / Heating View Scheme

1: n-BuLi / 1.) ether, -78 deg C - -40 deg C; 2.) -40 deg C - 0 deg C 2: 69 percent / 2,4-Dinitrobenzenesulfenyl chloride, NEt3 / CH2Cl2 / 1 h / 25 °C 3: m-Chloroperbenzoic acid (85percent), NaHCO3 / CCl4; H2O / 1 h / 0 °C 4: 1.) NBS; 2.) 1,5-Diazabicyclo<5.4.0>undec-5-ene / 1.) CCl4, reflux, 1 h, sunlamp; 2.) CH2Cl2, 25 deg C, 0.5 h 5: pyridine / 0.17 h / Heating View Scheme

1: m-Chloroperbenzoic acid (85percent), NaHCO3 / CCl4; H2O / 1 h / 0 °C 2: 1.) NBS; 2.) 1,5-Diazabicyclo<5.4.0>undec-5-ene / 1.) CCl4, reflux, 1 h, sunlamp; 2.) CH2Cl2, 25 deg C, 0.5 h 3: pyridine / 0.17 h / Heating View Scheme

1: 69 percent / 2,4-Dinitrobenzenesulfenyl chloride, NEt3 / CH2Cl2 / 1 h / 25 °C 2: m-Chloroperbenzoic acid (85percent), NaHCO3 / CCl4; H2O / 1 h / 0 °C 3: 1.) NBS; 2.) 1,5-Diazabicyclo<5.4.0>undec-5-ene / 1.) CCl4, reflux, 1 h, sunlamp; 2.) CH2Cl2, 25 deg C, 0.5 h 4: pyridine / 0.17 h / Heating View Scheme

1: 1.) NBS; 2.) 1,5-Diazabicyclo<5.4.0>undec-5-ene / 1.) CCl4, reflux, 1 h, sunlamp; 2.) CH2Cl2, 25 deg C, 0.5 h 2: pyridine / 0.17 h / Heating View Scheme

in pyridine 0.166667 h; Heating;

n-butyllithium; triphenylphosphine; zinc dibromide; bis(dibenzylideneacetone)-palladium(0) Yield given. Multistep reaction;

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