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ChemicalBook CAS DataBase List Phenyl sulfoxide
945-51-7

Phenyl sulfoxide synthesis

9synthesis methods
-

Yield:945-51-7 95% ,127-63-9 5%

Reaction Conditions:

with sodium hypochlorite pentahydrate in water;acetonitrile at 20; for 0.416667 h;Green chemistry;

Steps:

Representative Procedure for the Synthesis of Sulfoxides through the Reaction of Sulfides with NaOCl·5H2O:

General procedure: To a solution of thioanisole (1a; 248 mg, 2.0 mmol) in MeCN (10 mL) and H2O (2 mL), NaOCl·5H2O (362 mg, 2.2 mmol) was added and the mixture was stirred at r.t. for 18 min. H2O (20 mL) and CHCl3 (15mL) were added, the organic layer was separated, and the aqueous phase was extracted with CHCl3 (3 × 15 mL). The extracts were dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane-EtOAc, 1:2 v/v) to provide methyl phenyl sulfoxide (2a; 275 mg, 98%) as colorless crystals. Methyl phenyl sulfone (3a; 6 mg, 2%) was also obtained as colorless crystals.

References:

Okada, Tomohide;Matsumuro, Hiroaki;Kitagawa, Saori;Iwai, Toshiaki;Yamazaki, Kento;Kinoshita, Yukari;Kimura, Yoshikazu;Kirihara, Masayuki [Synlett,2015,vol. 26,# 18,art. no. ST-2015-U0520-L,p. 2547 - 2552]

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