ChemicalBook CAS DataBase List 4-CYANOBENZENESULFONYL CHLORIDE 97

4-CYANOBENZENESULFONYL CHLORIDE 97 synthesis

7synthesis methods

Product Name:4-CYANOBENZENESULFONYL CHLORIDE 97
CAS Number:49584-26-1
Molecular formula:C7H4ClNO2S
Molecular Weight:201.63

36801-01-1 Synthesis

36801-01-1
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49584-26-1
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Yield:49584-26-1 99%

Reaction Conditions:

with N-chloro-succinimide;isopropyl alcohol in dichloromethane at 0 - 20; for 1 h;

Steps:

General procedure for the preparation of sulfonyl halides from thiols
General procedure: To a stirred solution of the corresponding thiol 1 (1 eq) [1]^a and isopropanol (CAS: 67-63-0) (2 eq) in dichloromethane [2] (0.15 M), N-bromosuccinimide (CAS: 128-08-5) or N-chlorosuccinimide (CAS: 128-09-6) (4 or 3.5 equiv) was added portion wise^1b at rt (in the case of NBS) or 0 °C (in the case of NCS). The reaction mixture is stirred at rt until starting material was not visible by TLC (approx. 1 h). Then, the mixture was diluted with cold, saturated NaHCO₃, and extracted with EtOAc (x4).^1c The combined organic extracts were dried over anh. Na₂SO₄ and concentrated in vacuo to afford the crude material. Filtration on a SiO₂ column or radial chromatography using mixtures of hexanes/ethyl acetate/acetone as eluents, yielded the pure sulfonyl halides 2 or 3.

References:

Silva-Cuevas, Carolina;Perez-Arrieta, Carlos;Polindara-García, Luis A.;Lujan-Montelongo, J. Armando [Tetrahedron Letters,2017,vol. 58,# 23,p. 2244 - 2247] Location in patent:supporting information

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150993-53-6 Synthesis