Hydrochloric Acid → Silane, (4-bromophenyl)tri-2-propenyl-

HRID 589219Notes

Reaction equation

HRID 589219 reaction equation
[Br-].[Br-].[C:3]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:8]=CC=C[CH:4]=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([SiH2:29]OCC(CC=C)CC=C)=[CH:25][CH:24]=1.[CH2:39]([Mg]Br)[CH:40]=[CH2:41].Cl.[CH3:45][CH2:46][CH2:47]CCC.C(OCC)(=O)C>O.C(OCC)C.ClCCl>[Br:22][C:23]1[CH:24]=[CH:25][C:26]([Si:29]([CH2:47][CH:46]=[CH2:45])([CH2:39][CH:40]=[CH2:41])[CH2:8][CH:3]=[CH2:4])=[CH:27][CH:28]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 12890784Triphenylphosphane dibromideHCID 21226206Ethyl acetate hexaneHCID 131727687HCID 131727687, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 11120361Silane, (4-bromophenyl)tri-2-propenyl-Yield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To triphenylphosphine dibromide (447.5 mg, 1.060 mmol), distilled dichloromethane (5 ml) was added under a nitrogen atmosphere and dissolved. Then a solution prepared by dissolving 1-bromo-4-(diallylethoxysilyl)benzene (11) (300 mg, 0.9637 mmol) into distilled dichloromethane (1.5 ml) was added and stirred at room temperature for 12 hours. After stirring, diethyl ether solution of 1M allylmagnesium bromide (1.156 ml, 1.156 mmol) was added dropwise and stirred at room temperature for 5 hours. The reacted mixture is cooled down to 0° C. and diluted with water to stop the reaction. 10% hydrochloric acid was added until salt was completely dissolved. The obtained organic layer was separated and the obtained water layer was extracted with dichloromethane. The collected organic layer was each washed with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order, and dried over anhydrous magnesium sulfate and then filtered and concentrated under reduced pressure, obtaining a crude product. The crude product was passed through a silica gel short column (eluent: hexane/ethyl acetate=10/1), obtaining 1-bromo-4-(triallylsilyl)benzene (12) (yield: 256.4 mg, yield (%): 87%).

Workup

  1. additionwas added under a nitrogen atmosphere
  2. dissolutiondissolved
  3. customThen a solution prepared
  4. distillationinto distilled dichloromethane (1.5 ml)
  5. additionwas added
  6. stirringAfter stirring
  7. stirringstirred at room temperature for 5 hours
  8. temperatureThe reacted mixture is cooled down to 0° C.
  9. customthe reaction
  10. dissolutionwas completely dissolved
  11. customThe obtained organic layer was separated
  12. extractionthe obtained water layer was extracted with dichloromethane
  13. washeach washed with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order
  14. dry with materialdried over anhydrous magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure
  17. customobtaining a crude product

Sources & evidence

ORD record
ord-b01aae580fdb41c1871ac6657ff2d595
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

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