Sodium Iodide → HCID 19437002, compound

HRID 1655995Notes

Reaction equation

HRID 1655995 reaction equation
[CH2:1]([Si:8]([CH2:11]Br)([CH3:10])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:13].[Na+]>CC(C)=O>[CH2:1]([Si:8]([CH2:11][I:13])([CH3:10])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 19437027HCID 19437027, compound

Product 1

HCID 19437002HCID 19437002, compoundYield 94,412.398%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl(bromomethyl)dimethylsilane [Colm, Earborn and Foad M. S., Malmond J. Organomet. Chem., 209, 13 (1981)] (12 g, 0.05 mmol) and sodium iodide (45 g, 0.3 mmol) are refluxed with stirring in acetone (500 ml) during 24 hours. The reaction mixture is cooled, filtered and the solvent is evaporated under reduced pressure. The residue is dissolved in ether and washed with water. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure to afford benzyl(iodomethyl)dimethylsilane (13.7 g, 5%) as a slightly yellow oil.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customthe solvent is evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in ether
  5. washwashed with water
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d5cdf194e5c4e90bfe85221d6d0c528
Source dataset
uspto-grants-1993_10
Patent number
US05252587

Reaction notes

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