1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 3: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 4: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 5: 61 percent / mercuric acetate / 2 h / Heating 6: 86 percent / ammonia, methanol / 10 h / Ambient temperature 7: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 8: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 9: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 10: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 11: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 25 deg C, 1 h 12: 51 percent / benzene; methanol / 16 h / Heating 13: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 14: hydrochloric acid / methanol View Scheme

1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 3: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 4: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 5: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 6: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 7: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 8: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 9: hexane; methanol / 14 h / Heating 10: hydrochloric acid / ethanol View Scheme

1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 3: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 4: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 5: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 6: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 7: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C View Scheme

1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 3: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 4: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 5: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 6: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 7: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 8: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 9: hexane; methanol / 14 h / Heating View Scheme

1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 3: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 4: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 5: 61 percent / mercuric acetate / 2 h / Heating 6: 86 percent / ammonia, methanol / 10 h / Ambient temperature 7: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 8: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 9: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 10: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 11: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 25 deg C, 1 h 12: 51 percent / benzene; methanol / 16 h / Heating 13: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr View Scheme

1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 3: 96 percent / triethylamine, 4-dimethylaminopyridine / CH2Cl2 / 8 h / 22 °C 4: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 5: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 6: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 7: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 8: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 9: hexane; methanol / 14 h / Heating 10: hydrochloric acid / ethanol 11: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '507140', constants.ctx, '0')"><i>N</i>,<i>N</i>-dimethyl-aniline</a> <br />T=193&deg;C;&nbsp;2.5&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1) potassium tert-butoxide / 1) tert-butyl alcohol, reflux, o.5 h, 2) tert-butyl alcohol, reflux, 8 h<br />2: 82 percent / N,N-dimethylaniline / 2.5 h / 193 &deg;C<br /> <br /> &nbsp;