Carbon Dioxide → HCID 59710676, compound

HRID 2221163Notes

Reaction equation

HRID 2221163 reaction equation
[Mg].[F:2][C:3]([O:7][C:8]1[CH:9]=[C:10](Br)[CH:11]=[CH:12][CH:13]=1)=[C:4]([F:6])[F:5].[CH2:15]([O:17][Si:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])Cl)[CH3:16].C(=O)=O>CCCCCCC.C(#N)C.O1CCCC1>[F:2][C:3]([O:7][C:8]1[CH:9]=[C:10]([Si:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])[O:17][CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=1)=[C:4]([F:6])[F:5]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 78398TriethoxychlorosilaneHCID 5462224MagnesiumHCID 59710681260262-38-2

Product 1

HCID 59710676HCID 59710676, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

Magnesium (0.12 mol) and tetrahydrofuran were put in a 2-bulb flask purged with nitrogen. Then, 3-[(trifluorovinyl)oxy]bromobenzene prepared in (2) was dropped very slowly maintaining the reactor temperature at 0° C. The reactor was put in an ice bath to prevent the temperature from rising rapidly. After adding 3-[(trifluorovinyl)oxy]bromobenzene, the reactor was heated to room temperature, and reaction was performed for 2 hours. Then, triethoxychlorosilane (0.95 mol) was dropped keeping the reactor temperature at −48° C. with a constant temperature bath filled with dry ice and acetonitrile. The reaction mixture was mixed at room temperature for 24 hours. After the reaction was completed, excess heptane was added to remove the obtained salt and unreacted magnesium. The filtrate was removed by filtering with filter paper. Heptane remaining in the filtrate was removed using a vacuum evaporator and vacuum-distilled to obtain [3-[(trifluorovinyl)oxy]phenyl]triethoxysilane (PFCBSI) (yield: 80%).

Workup

  1. custompurged with nitrogen
  2. customThen, 3-[(trifluorovinyl)oxy]bromobenzene prepared in (2)
  3. additionwas dropped very slowly
  4. customThe reactor was put in an ice bath
  5. temperaturethe reactor was heated to room temperature
  6. customreaction
  7. customat −48° C.
  8. additionThe reaction mixture was mixed at room temperature for 24 hours
  9. customto remove the obtained salt and unreacted magnesium
  10. customThe filtrate was removed
  11. filtrationby filtering
  12. filtrationwith filter paper
  13. customHeptane remaining in the filtrate was removed
  14. customa vacuum evaporator
  15. distillationvacuum-distilled

Sources & evidence

ORD record
ord-0a7f19f08dc74087ac5562ff58253181
Source dataset
uspto-grants-2008_05
Patent number
US07368514B2

Reaction notes

Loading…