Chloromethyl phenyl sulfone

100-68-5

3112-85-4

7205-98-3

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.