1,2-Dibromoethane → HCID 15332486, compound

HRID 1440992Notes

Reaction equation

HRID 1440992 reaction equation
[Mg].BrCCBr.Cl[CH2:7][Si:8]([CH3:16])([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].[Cl-].[NH4+]>C(OCC)C.O.[Cu]Br>[CH3:15][Si:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:16])[CH2:7][CH2:19][CH2:18][C:17]([O:21][CH2:22][CH3:23])=[O:20]

Participants

9

Reactant 5

HCID 78391,2-DibromoethaneHCID 8821Ethyl AcrylateHCID 25517Ammonium ChlorideHCID 74598(Chloromethyl)dimethylphenylsilaneHCID 5462224Magnesium

Product 1

HCID 15332486HCID 15332486, compoundYield 47.9%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent4×

Conditions

Temperature
-10 °C

Procedure

To a stirred mixture of 7.9 g (0.329 mole) of magnesium metal and 0.5 mL of 1,2-dibromoethane in 150 mL of diethyl ether was added dropwise a solution of 50 g (0.271 mole) of (chloromethyl)dimethylphenylsilane in 100 mL of diethyl ether. The addition required 30 minutes. Upon completion of addition, the resultant solution was transferred using a cannula to a flask containing 15.5 g (0.108 mole) of copper(I) bromide which was under a nitrogen atmosphere and was cooled in a dry ice/acetone bath. To this flask was added dropwise a solution 10.8 g (0.108 mole) of ethyl acrylate in 50 mL of diethyl ether. The addition required 40 minutes. Upon completion of addition, the reaction mixture was allowed to warm to -10° C. It was then diluted with 400 mL of diethyl ether, and a solution of 14.2 g of ammonium chloride in 40 mL of water was added dropwise while maintaining the temperature at -10° C. to 0° C. Upon completion of addition, the reaction mixture was filtered, and the solvent was evaporated under reduced pressure, leaving a residue. This residue was passed through a column of silica gel, eluting with diethyl ether/petroleum ether (5:95). The product-containing fractions were combined, and the solvent was evaporated, yielding 12.95 g of ethyl 5-methyl-5-phenyl-5-silahexanoate as an oil.

Workup

  1. additionThe addition required 30 minutes
  2. additionUpon completion of addition
  3. temperaturewas cooled in a dry ice/acetone bath
  4. additionThe addition required 40 minutes
  5. additionUpon completion of addition
  6. temperaturewhile maintaining the temperature at -10° C. to 0° C
  7. additionUpon completion of addition
  8. filtrationthe reaction mixture was filtered
  9. customthe solvent was evaporated under reduced pressure
  10. customleaving a residue
  11. washeluting with diethyl ether/petroleum ether (5:95)
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9a87d0da5f3f4e098d25e8e0cebbdfe6
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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