1: methanol 2: K2CO3; methanol / 7 °C View Scheme

1: bromine / 1.) benzene, 0 deg C, 1 h, dark, 2.) sunlight, 15 min 2: 4 percent / tributylstannane, azodiisobutyronitrile / benzene / 15 h / 60 °C View Scheme

1.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 1.2: tetrahydrofuran / 0.5 h / 25 °C 2.1: 30 percent / 650 °C / 0.75 - 3 Torr View Scheme

aluminium amalgam in tetrahydrofuran; water 0.666667 h; Heating;

1: SOCl2 / 3 h / Heating 2: 98.2 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 3: 87.6 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 4: 91.6 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 5: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 6: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1: 98.2 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 87.6 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 3: 91.6 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 4: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 5: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1: 87.6 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 2: 91.6 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 3: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 4: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1: 91.6 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 2: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 3: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 2: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 2.1: methanol; water; sodium hydroxide / 5 h / Reflux 2.2: 1 h / Reflux 3.1: iodine; potassium hydroxide / -5 - 0 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 5.1: methanol; water; sodium hydroxide / 5 h / Reflux 5.2: 1 h / Reflux 6.1: iodine; potassium hydroxide / -5 - 0 °C 7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 8.1: methanol; water; sodium hydroxide / 5 h / Reflux 8.2: 1 h / Reflux 9.1: iodine; potassium hydroxide / -5 - 0 °C 10.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 11.1: methanol; water; sodium hydroxide / 5 h / Reflux 11.2: 1 h / Reflux 12.1: iodine; potassium hydroxide / -5 - 0 °C 13.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 14.1: methanol; water; sodium hydroxide / 5 h / Reflux 14.2: 1 h / Reflux 15.1: iodine; potassium hydroxide / -5 - 0 °C 16.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 17.1: methanol; water; sodium hydroxide / 5 h / Reflux 17.2: 1 h / Reflux 18.1: iodine; potassium hydroxide / -5 - 0 °C 19.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 20.1: methanol; water; sodium hydroxide / 5 h / Reflux 20.2: 1 h / Reflux View Scheme