Citric Acid → 3-bromopropyltriallylsilane

HRID 589221Notes

Reaction equation

HRID 589221 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][Si:5](Cl)(Cl)Cl.[CH2:9]([Mg]Br)[CH:10]=[CH2:11].C(OCC)C.C(O)(=O)C[C:21]([CH2:26][C:27](O)=O)(C(O)=O)O.[CH3:32][CH2:33][CH2:34]CCC>>[CH2:9]([Si:5]([CH2:27][CH:26]=[CH2:21])([CH2:34][CH:33]=[CH2:32])[CH2:4][CH2:3][CH2:2][Br:1])[CH:10]=[CH2:11]

Participants

6

Reactant 5

HCID 311Citric AcidHCID 3283Diethyl EtherHCID 8058HexaneHCID 83792Silane, (3-bromopropyl)trichloro-HCID 178455850HCID 178455850, compound

Product 1

HCID 110330293-bromopropyltriallylsilaneYield 98%

Procedure

Under a nitrogen atmosphere, (3-bromopropyl)trichlorosilane (22) (1 equiv., 5 g, 19.5 mmol) was cooled down to 0° C., then 1M allylmagnesium bromide solution (3.3 equiv., 64.5 ml) was added and stirred at room temperature for 3 hours. To the reacted mixture, diethyl ether was added and neutralized with aqueous solution of citric acid. The obtained water layer was extracted with diethyl ether and the collected organic layer was washed with saturated saline solution, then dried over anhydrous magnesium sulfate and filtered, concentrated under reduced pressure, obtaining a crude product. The crude product was passed through silica gel column chromatography (eluent: n-hexane), obtaining triallyl(3-bromopropyl)silane (23) represented by the following chemical reaction equation (yield: 5.2 g, yield (%): 98%).

Workup

  1. extractionThe obtained water layer was extracted with diethyl ether
  2. washthe collected organic layer was washed with saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customobtaining a crude product

Sources & evidence

ORD record
ord-92d9e12a0fdc4ccabae105731fff4851
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

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