反应详情

Combine methyl 2-methoxy-5-methylthiobenzoate (3.0 g, 14.1 mmol), pyridine (10 mL) and water (10 mL). Cool in an ice bath. Add portionwise phenyltrimethylammonium tribromide (5.84 g, 15.5 mmol). After 30 minutes, warm to ambient temperature. After 3 hour, add a solution of sodium bisulfite (1.6 g) in water (4 mL). After 10 minutes, add a 12 M aqueous hydrochloric acid solution (11 mL) and water. Extract the reaction mixture four times with dichloromethane. Combine the organic layers, extract with brine, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give methyl 2-methoxy-5-methylsulfinylbenzoate: mp; 64-66° C. Elemental Analysis calculated for C9H12O4S: C, 52.62; H, 5.30. Found: C, 52.51; H, 5.37.

1. temperatureCool in an ice bath
2. waitAfter 3 hour
3. waitAfter 10 minutes
4. extractionExtract the reaction mixture four times with dichloromethane
5. extractionextract with brine
6. dry with materialdry over Na2SO4
7. filtrationfilter
8. customevaporate in vacuo
9. customto give a residue