Iodine → (1-Fluorovinyl)methyldiphenylsilane

HRID 660362

Reaction equation

HRID 660362 reaction equation
[Li].[CH3:2][Si:3](Cl)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.II.[F:19][C:20](F)=[CH2:21]>O1CCCC1>[F:19][C:20]([Si:3]([CH3:2])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:21]

Participants

6

Reactant 4

HCID 807IodineHCID 6369Vinylidene fluorideHCID 67349Chloro(methyl)diphenylsilaneHCID 3028194Lithium

Product 1

HCID 10922738(1-Fluorovinyl)methyldiphenylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium wire (2.08 g, 300 mmol) in dry tetrahydrofuran (150 ml) was added methyldiphenylsilyl chloride (15.8 ml, 75 mmol) and a catalytic amount of iodine. The reaction mixture was sonicated for 40 min and then stirred overnight at room temperature. The reaction mixture was cooled to −78° C. and 1,1-difluoroethylene (approx. 225 mmol) was passed through the mixture for 30 min. The mixture was stirred at −78° C. for 2 h and then warmed to room temperature.

Workup

  1. customThe reaction mixture was sonicated for 40 min
  2. temperatureThe reaction mixture was cooled to −78° C.
  3. stirringThe mixture was stirred at −78° C. for 2 h
  4. temperaturewarmed to room temperature

Sources & evidence

ORD record
ord-feeafb9a18b546f9a22aa6526051900c
Source dataset
uspto-grants-2011_12
Patent number
US08084486B2

Linked notes

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