1,4-Dibromobenzene → HCID 54226218, compound

HRID 463791Notes

Reaction equation

HRID 463791 reaction equation
[CH2:1]([Si:3]([CH3:10])([O:7][CH2:8][CH3:9])OCC)[CH3:2].[Mg].Br[C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=1>O1CCCC1>[CH2:1]([Si:3]([CH3:10])([O:7][CH2:8][CH3:9])[C:13]1[CH:18]=[CH:17][C:16]([Si:3]([CH2:1][CH3:2])([CH3:10])[O:7][CH2:8][CH3:9])=[CH:15][CH:14]=1)[CH3:2]

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 5462224MagnesiumHCID 13561453HCID 13561453, compound

Product 1

HCID 54226218HCID 54226218, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

16.2 g of ethylmethyldiethoxysilane, 2.43 g of magnesium and 10 ml of tetrahydrofuran were charged into a 500-ml, three-necked flask provided with a stirrer, a cooler and a dropping funnel and stirred under a nitrogen gas stream, while 100 ml of a tetrahydrofuran solution containing 11,8 g of p-dibromobenzene was dropwise added thereto from the dropping funnel over about 3 hours. After the dropwise addition, the mixture was further stirred and refluxed for about 5 hours. After the refluxing, the resulting polymer was separated by filtration, and then the solvent was removed therefrom by distillation. The residues were then subjected to distillation under reduced pressure, whereby 10.5 g of p-bis(ethylmethylethoxysilyl)benzene was obtained (yield: 68%, boiling point: 122°-125° C./3 mmHg).

Workup

  1. customprovided with a stirrer
  2. additionwas dropwise added
  3. additionAfter the dropwise addition
  4. stirringthe mixture was further stirred
  5. temperaturerefluxed for about 5 hours
  6. customAfter the refluxing, the resulting polymer was separated by filtration
  7. customthe solvent was removed
  8. distillationby distillation
  9. distillationThe residues were then subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-b264f9c9608242a19136c31ef06fcd73
Source dataset
uspto-grants-1985_10
Patent number
US04544729

Reaction notes

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