ChemicalBook CAS DataBase List o-Toluenesulfonyl fluoride

o-Toluenesulfonyl fluoride synthesis

9synthesis methods

Product Name:o-Toluenesulfonyl fluoride
CAS Number:444-31-5
Molecular formula:C7H7FO2S
Molecular Weight:174.19

133-59-5 Synthesis

133-59-5
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444-31-5
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Yield:444-31-5 92%

Reaction Conditions:

with Tripropylamine;sulfuryl fluoride in acetone at 20; for 2 h;Inert atmosphere;

Steps:

3. General Procedure for Aryl Sulfonyl Fluorides Synthesis

General procedure: An oven-dried reaction flask (30 mL) equipped with a stirring bar was charged with aryl sulfonyl chloride (1, 2 mmol), n-Pr₃N (6.0 mmol, 860 mg, 3.0 equiv.) and THF (10 mL). Then the flask was covered with a plastic stopper before the sulfuryl fluoride gas (SO₂F₂) was introduced into the mixture by slowly bubbling from a SO₂F₂ balloon. The air in the flask was excluded by SO₂F₂ gas for about 10 seconds and the resulting mixture was subsequently allowed to stir at room temperature for 2 h. Once the reaction reached its completion, the mixture was diluted with water and the aqueous phrase was extracted with EtOAc (20 mL 3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to dryness under vacuum. The residue was purified through flash silica gel chromatography using a mixture of ethyl acetate and petroleum ether as eluent to afford the desired aryl sulfonyl fluoride 2.

References:

He, Yunlu;Liu, Qiang;Pan, Xi;Peng, Sanwen;Qin, Hua-Li;Song, Xuyan;Tang, Haolin;Wang, Bo;Wei, Min [Tetrahedron,2022,vol. 108,art. no. 132657] Location in patent:supporting information

88-19-7 Synthesis