Chlorotrifluoroethylene → 1,2,2-Trifluoroethenyl-triethylsilane

HRID 1979623Notes

Reaction equation

HRID 1979623 reaction equation
C(=O)=O.C(O)C.Cl[C:8]([F:12])=[C:9]([F:11])[F:10].Cl[Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16].C([Li])CCC>C1COCC1>[CH2:15]([Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[C:8]([F:12])=[C:9]([F:11])[F:10])[CH3:16]

Participants

6

Reactant 4

HCID 6594ChlorotrifluoroethyleneHCID 13819ChlorotriethylsilaneHCID 19604758Methanedione--ethanol (1/1)HCID 178418339Butyllithium

Product 1

HCID 109214661,2,2-Trifluoroethenyl-triethylsilaneYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A reactor flushed with argon gas was cooled with a dry ice-ethanol cooling medium, and 2.03 g (0.0174 mol) of chlorotrifluoroethylene was introduced into the reactor. To this reactor, 17 ml of THF was introduced to bring the chlorotrifluoroethylene concentration to 1 mmol/ml, and then 2.35 g (0.016 mol) of chlorotriethylsilane was added. The reactor was cooled to -78° C., and 12 ml (0.018 mol) of butyllithium (1.47M hexane solution) was added in 1 hour. The mixture was stirred at 78° C. for 4 hours and at room temperature for about 1 hour. Workup was conducted in the same manner as in Example 1, whereby 2.64 g (86.2%) of triethyltrifluorovinylsilane was obtained.

Workup

  1. customA reactor flushed with argon gas
  2. additionwas introduced into the reactor
  3. concentrationthe chlorotrifluoroethylene concentration to 1 mmol/ml

Sources & evidence

ORD record
ord-416e37cab6ca48c594168148fdc0528c
Source dataset
uspto-grants-1984_11
Patent number
US04481366

Reaction notes

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