Uses
Chloromethyl Phenyl Sulfone is used to synthesis of α,β-epoxy sulfones and aziridines; reacts with electrophilic arenes, heterocyclic arenes, and
alkenes; source of the α-phenylsulfonylmethyl radical.
Preparation
Preparative Methods of Chloromethyl Phenyl Sulfone: several methods are available. The most convenient is the reaction of Sodium
Benzenesulfinate dihydrate with bromochloromethane in dimethyl sulfoxide.
Synthesis
The general procedure for the synthesis of phenylmethyl sulfone and chloromethyl phenyl sulfone from methyl phenyl sulfide was as follows: 0.25 g (2 mmol) of methyl phenyl sulfide was used as a substrate and added to a 50 mL three-necked flask along with 10 mL of acetonitrile and 2 mL of water. The internal temperature of the flask was maintained at 23 °C. Subsequently, 0.09 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals were added in portions with continuous stirring. During the reaction, the internal temperature of the flask was increased to 28°C and then gradually decreased. GC analysis was performed 3 h after the start of the reaction and showed that 22% of the methyl phenyl sulfide was converted to methyl phenyl sulfoxide and 65% to methyl phenyl sulfone. By-products included 6% chloromethyl phenyl sulfoxide and 7% chloromethyl phenyl sulfone, and a total of 0.8% advanced chlorides. Addition of 0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was continued and stirring was continued for 1 hour. At this point, the methyl phenyl sulfide and methyl phenyl sulfoxide completely disappeared and the yield of methyl phenyl sulfone increased to 87%. Impurities included 11% chloromethyl phenyl sulfone, 0.5% dichloromethyl phenyl sulfone and 1.3% trichloromethyl phenyl sulfone.
Solubility in organics
Chloromethyl Phenyl Sulfone is soluble in THF, CHCl3, CH2Cl2, and most organic solvents.
References
[1] Patent: JP2017/52730, 2017, A. Location in patent: Paragraph 0046
