Carbon Dioxide → Methyl 2,2,3,3-tetrafluoro-3-(methylsulfanyl)propanoate

HRID 1735388Notes

Reaction equation

HRID 1735388 reaction equation
C[S-].[Na+].C[S:5]([CH3:7])=O.[F:8][C:9]([F:13])=[C:10]([F:12])[F:11].COS([O:19][CH3:20])(=O)=O.[C:21](=O)=[O:22]>>[CH3:7][S:5][C:9]([C:10]([C:21]([O:19][CH3:20])=[O:22])([F:12])[F:11])([F:13])[F:8]

Participants

6

Reactant 5

HCID 280Carbon Dioxide2×HCID 679Dimethyl Sulfoxide2×HCID 6497Dimethyl SulfateHCID 8301TetrafluoroethyleneHCID 4378561Sodium methanethiolate

Product 1

HCID 13328904Methyl 2,2,3,3-tetrafluoro-3-(methylsulfanyl)propanoate

Conditions

Temperature
100 °C

Procedure

A 400 mL pressure vessel was charged with 34.1 g (0.49 mol) of sodium thiomethoxide and 150 mL of anhydrous dimethylsulfoxide (DMSO). The vessel was closed, cooled in dry ice, evacuated and charged with 32 g (0.73 mol) of carbon dioxide and 50 g (0.5 mol) of tetrafluoroethylene. The vessel contents were heated with agitation to 50° C. for 1 hr and 100° C. for 5 hr. After cooling to room temperature, the vessel contents were transferred to a 500 mL round bottom flask using an additional 30 mL of DMSO to rinse. Dimethylsulfate (65 g, 0.52 mol) was added and the mixture was stirred for 3 hr at 30°-50° C. Volatiles were removed by distillation at 1 mm into a dry ice cooled receiver with a maximum pot temperature of 65 ° C.

Workup

  1. customThe vessel was closed
  2. customevacuated
  3. temperatureAfter cooling to room temperature
  4. customthe vessel contents were transferred to a 500 mL round bottom flask
  5. washto rinse
  6. customVolatiles were removed by distillation at 1 mm into a dry ice cooled receiver with a maximum pot temperature of 65 ° C.

Sources & evidence

ORD record
ord-19707aa8efa64412a40eaa08b1f1820b
Source dataset
uspto-grants-1996_07
Patent number
US05536754

Reaction notes

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