Dichlorodimethylsilane → HCID 22902837, compound

HRID 1489883Notes

Reaction equation

HRID 1489883 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.[Cu](C#N)C#N.Cl[Si:16](Cl)([CH3:18])[CH3:17].[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1Br>BrCCBr.CCOCC>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([Si:16]([C:24]2[CH:25]=[CH:26][C:21]([Br:20])=[CH:22][CH:23]=2)([CH3:18])[CH3:17])=[CH:4][CH:5]=1

Participants

8

Reactant 5

HCID 6398DichlorodimethylsilaneHCID 78041,4-DibromobenzeneHCID 114141,2-DibromobenzeneHCID 5462224Magnesium2×HCID 178418260HCID 178418260, compound

Product 1

HCID 22902837HCID 22902837, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

A 100 mL three-neck flask was equipped with an addition funnel, condenser, and stir bar. The flask was flame dried, flushed with argon and charged with magnesium (1.04 g, 42.8 mmol) and 5 mL of dry ether. A few drops of 1,2-dibromoethane was added to activate the magnesium and caused the ether to reflux. p-Dibromobenzene (10 g, 42.4 mmol) in 40 mL of ether was added dropwise at such a rate as to maintain reflux. After complete addition, the reaction mixture was heated to maintain reflux for an additional five hours. Upon cooling to room temperature copper cyanide (0.1 g, 1.1 mmol) was introduced. The reaction mixture was then cooled to 0 C. and dichlorodimethylsilane (2.55 g, 19.8 mmol) was added dropwise through the addition funnel causing the reaction to warm slightly. The reaction mixture was stirred overnight at room temperature. The product mixture was poured over ice and the organic layer was separated and dried over anhydrous sodium sulfate. The ether was removed by vacuum and a yellow oily solid was recovered. The crude product (5c) was fractionally sublimed under full vacuum. The first fraction contained non-reacted dibromobenzene and 2.6 g (36% yield) of 5c was collected for the second fraction. 1 H NMR (in CDCl3): d, 7.47 ppm 4H; d, 7.32 ppm 4H; s, 0.51 ppm 6H.

Workup

  1. customA 100 mL three-neck flask was equipped with an addition funnel, condenser
  2. temperatureThe flask was flame
  3. customdried
  4. customflushed with argon
  5. temperatureto reflux
  6. temperatureto maintain
  7. temperaturereflux
  8. additionAfter complete addition
  9. temperaturethe reaction mixture was heated
  10. temperatureto maintain
  11. temperaturereflux for an additional five hours
  12. additionwas introduced
  13. temperatureThe reaction mixture was then cooled to 0 C
  14. customthe reaction
  15. temperatureto warm slightly
  16. stirringThe reaction mixture was stirred overnight at room temperature
  17. additionThe product mixture was poured over ice
  18. customthe organic layer was separated
  19. dry with materialdried over anhydrous sodium sulfate
  20. customThe ether was removed by vacuum
  21. customa yellow oily solid was recovered

Sources & evidence

ORD record
ord-d7e833a736434f53b9c37b5108016c32
Source dataset
uspto-grants-1997_10
Patent number
US05679818

Reaction notes

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