ChemicalBook CAS DataBase List (4-Nitrophenyl)methanesulfonyl chloride

(4-Nitrophenyl)methanesulfonyl chloride synthesis

13synthesis methods

Product Name:(4-Nitrophenyl)methanesulfonyl chloride
CAS Number:4025-75-6
Molecular formula:C7H6ClNO4S
Molecular Weight:235.64

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Yield: 88%

Reaction Conditions:

with tert-butylhypochlorite in water;acetonitrile at 0 - 20;

Steps:

Sulfonyl Chlorides 3; General Procedure
General procedure: Alkyl halide (or sulfate) (5 mmol) and thiourea (0.381 g, 5 mmol) were heated at reflux in EtOH (5 mL) for 1 h. After removal of the solvent in vacuum and washing with Et₂O (3 × 5 mL), the corresponding S-alkyl isothiourea salt was obtained as a white solid in almost quantitative yield. Without purification, the product was transferred into a three-necked round-bottom flask equipped with a thermometer and an addition funnel in an ice-bath, followed by addition of water (0.45mL) and MeCN (10 mL). To the resultant vigorously stirred mixture was added dropwise a solution of t-BuOCl (2.86 mL) in MeCN (5 mL), keeping the inner temperature at 0-20 °C. The mixture was then stirred for 30 min. Removal of the solvent under vacuum, addition of Et₂O (15 mL), washing with H₂O (2 × 10 mL), drying over Na₂SO₄, and concentration under vacuum gave the desired product in high purity. The product was further purified by recrystalization from petroleum ether-EtOAc.

References:

Qiu, Kui;Wang, Rennan [Synthesis,2015,vol. 47,# 20,art. no. SS-2015-H0078-OP,p. 3186 - 3190]