Sodium Iodide → Iodopropyldimethylvinylsilane

HRID 1170069

Reaction equation

HRID 1170069 reaction equation
Cl[CH2:2][CH2:3][CH2:4][SiH2:5][CH:6]=[C:7]([CH3:9])[CH3:8].[I-:10].[Na+]>CC(CC)=O>[I:10][CH2:2][CH2:3][CH2:4][SiH2:5][CH:6]=[C:7]([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131715857Chloropropyldimethylvinylsilane

Product 1

HCID 131728415IodopropyldimethylvinylsilaneYield 53.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
75 °C

Procedure

To a stirring solution of chloropropyldimethylvinylsilane (645 g) in ethyl methyl ketone (4.65 L), sodium iodide (1.215 Kg) was added under nitrogen and the mixture heated at 75° C. for 24 hr. The reaction mixture was cooled and added D.M. Water (1.62 L) and separated organic layer. The aqueous layer was re-extracted with ethyl methyl ketone (1.16 L) and the extract combined with the organic layer. The organic layer was dried on sodium sulfate and evaporated to dryness. Orange oil was purified by vacuum distillation to give colourless liquid the title product (540 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionadded D.M
  3. customWater (1.62 L) and separated organic layer
  4. extractionThe aqueous layer was re-extracted with ethyl methyl ketone (1.16 L)
  5. customThe organic layer was dried on sodium sulfate
  6. customevaporated to dryness
  7. distillationOrange oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-8205c8f0b2644da4b9373ef46ef7c4f7
Source dataset
uspto-grants-2010_11
Patent number
US07825257B1

Linked notes

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