2-Ethoxy-benzenesulfonyl chloride synthesis

Yield: 42%

Reaction Conditions:

Stage #1:Phenetole with n-butyllithium;N,N,N,N,-tetramethylethylenediamine in diethyl ether at 0; for 1 h;
Stage #2: with sulfur dioxide in diethyl ether at -78 - 20; for 1.5 h;
Stage #3: with thionyl chloride in diethyl ether at 20; for 6 h;

Steps:

112.1; 191.1 (Step 1) 2-Ethoxybenzenesulfonyl Chloride
Tetramethylethylenediamine (15.2 ml, 101 mmol) was dissolved in diethyl ether (200 ml). After the solution was cooled to 0° C., n-butyllithium (2.5 mol/l, 40.0 ml, 100 mmol) was added thereto, followed by stirring for 5 minutes. To the reaction liquid, ethoxybenzene (11.0 ml, 87.1 mmol) was added, followed by stirring for further 1 hour. The reaction liquid was cooled to -78° C., and sulfur dioxide was added with a syringe over 30 minutes. After that, the temperature was raised to room temperature with stirring over 1 hour. To the reaction liquid, thionyl chloride (8.80 ml, 110 mmol) was added, followed by stirring at room temperature for 6 hours. The reaction liquid was diluted with diethyl ether, and washed with water and saturated aqueous sodium chloride. Then, the organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain the title compound (8.1 g, 42%).

References:

AJINOMOTO CO., LTD.;Ueno, Hirokazu;Yamamoto, Takashi;Takashita, Ryuta;Yokoyama, Ryohei;Sugiura, Toshihiko;Kageyama, Shunsuke;Ando, Ayatoshi;Eda, Hiroyuki;Eviryanti, Agung;Miyazawa, Tomoko;Kirihara, Aya;Tanabe, Itsuya;Nakamura, Tarou;Noguchi, Misato;Shuto, Manami;Sugiki, Masayuki;Dohi, Mizuki US2015/51395, 2015, A1 Location in patent:Paragraph 0725; 1194