Chlorotrimethylsilane → 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene

HRID 985740Notes

Reaction equation

HRID 985740 reaction equation
[Mg].Cl[Si:3]([CH3:6])([CH3:5])[CH3:4].[F:7][C:8](F)([F:17])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]>O1CCCC1>[F:7][C:8]([F:17])=[C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[O:10][Si:3]([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 99052,2,2-Trifluoroacetophenone2×HCID 5462224Magnesium

Product 1

HCID 108896672,2-difluoro-1-phenyl-1-trimethylsiloxyetheneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a dry 250 ml Schlenk flask the following compounds were added: magnesium turnings (1.45 g, 60 mmol), dry tetrahydrofuran (THF, 120 ml) and chlorotrimethylsilane (TMSCl, 13.0 g, 120 mmol). The flask was cooled to 0° C. 2,2,2-Trifluoroacetophenone (non-radioactive) 2a (5.2 g, 30 mmol) was added drop wise into the flask with a syringe. After addition of the 2,2,2-Trifluoroacetophenone, the reaction mixture was stirred for an additional 1 h. The completion of the reaction was monitored by 19F NMR spectroscopy. The solvent and excess TMSCl were removed under vacuum, and hexane (50 ml) was added to the residue. Solid impurities were removed by suction filtration, and the solvent was evaporated to yield 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene 1a (6.8 g, 99% yield).

Workup

  1. additionTo a dry 250 ml Schlenk flask the following compounds were added
  2. customThe solvent and excess TMSCl were removed under vacuum, and hexane (50 ml)
  3. additionwas added to the residue
  4. customSolid impurities were removed by suction filtration
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a662779651e54725bba1c0f37ecc55e2
Source dataset
uspto-grants-2005_03
Patent number
US06872855B1

Reaction notes

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