Reaction #478779

Reaction equation

K2CO3

methyl 3-(methylsulfinyl)benzoate

2,2,2-trifluoroacetamide

magnesium oxide

iodobenzene diacetate

→

title compound

Yield 74.2%

Methyl 3-(S-methylsulfonimidoyl)benzoate

Yield 74.2%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Filtrationthe mixture was filtered
2. 2
   Filtrationpast filter agent (Celite)
3. 3
   Washrinsed with chloroform, and rotary evaporated
4. 4
   workup.DISSOLUTIONThe sample was dissolved in EtOAc
5. 5
   Washwashed with brine/dilute HCl, brine
6. 6
   Dryingdried with anhydrous Na2SO4 and rotary evaporated
7. 7
   workup.DISSOLUTIONThe yellow-orange oil was dissolved in 60 ml MeOH
8. 8
   OtherThe MeOH filtrate was decanted from the solids, which
9. 9
   Washwere then rinsed with MeOH and EtOAc
10. 10
    workup.ADDITIONthe aqueous layer diluted
11. 11
    workup.ADDITIONby adding H2O
12. 12
    WashThe aqueous layer was washed with 30% EtOAc in hexane
13. 13
    ExtractionThe aqueous layer was extracted with CHCl3
14. 14
    Washthe combined CHCl3 layers washed with brine
15. 15
    Dryingdried with anhydrous Na2SO4
16. 16
    Otherrotary evaporated

Procedure

A solution of methyl 3-(methylsulfinyl)benzoate (3.23 g, 16.3 mmol), 2,2,2-trifluoroacetamide (3.69 g, 32.6 mmol), magnesium oxide (1.97 g, 48.9 mmol), rhodium(II)acetate dimer (0.18 g, 0.408 mmol), and iodobenzene diacetate (7.88 g, 24.5 mmol) in 150 ml dichloromethane was stirred at room temperature. After 16 hours, the mixture was filtered past filter agent (Celite), rinsed with chloroform, and rotary evaporated. The sample was dissolved in EtOAc, washed with brine/dilute HCl, brine, dried with anhydrous Na2SO4 and rotary evaporated. The yellow-orange oil was dissolved in 60 ml MeOH, K2CO3 (6.76 g, 48.9 mmol) added, and the mixture stirred at room temperature for 12 minutes. The MeOH filtrate was decanted from the solids, which were then rinsed with MeOH and EtOAc. The pH of the combined organic filtrates were adjusted to pH 2 using 4% HCl, then the aqueous layer diluted by adding H2O. The aqueous layer was washed with 30% EtOAc in hexane, then the pH adjusted to pH 9 with saturated Na2CO3. The aqueous layer was extracted with CHCl3, the combined CHCl3 layers washed with brine, dried with anhydrous Na2SO4 and rotary evaporated to give the title compound as a light tan solid (2.58 g, 74%).

Source