2-Bromostyrene → HCID 57911422, compound

HRID 1666131Notes

Reaction equation

HRID 1666131 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH2:9].[Li]CCCC.[CH:15](=[O:20])[CH2:16][CH2:17][CH:18]=[CH2:19].Cl[Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24]>C1COCC1.C1C=CC=CC=1>[CH:23]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[O:20][CH:15]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH2:9])[CH2:16][CH2:17][CH:18]=[CH2:19])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 162642-BromostyreneHCID 164184-PentenalHCID 139400Triisopropylsilyl chlorideHCID 178418339Butyllithium

Product 1

HCID 57911422HCID 57911422, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1-Bromo-2-vinylbenzene (2.8146 g, 15.38 mmol) was azeotropped by dry benzene twice before taken up in THF (50 ml). The solution was cooled to −78° C. BuLi (6.77 ml, 16.91 mmol) was added to the reaction mixture at −78° C. and stirred for 20 min at this temperature. pent-4-enal (1.670 ml, 16.91 mmol) was added to the reaction mixture and stirred for 4 hours while the bath temperature gradually warmed up. Chlorotriisopropylsilane (3.58 ml, 16.91 mmol) was added to the reaction mixture and the reaction was stirred overnight while the reaction was warmed up to room temperature. The solvent was mostly removed via vacuum and the crude was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried (Na2SO4), filtered and concentrated. The product was obtained by flash column eluted with ether in hexane from 0 to 30% (3.9 g, 74% yield). MS(ESI)[M+H+]=346.46.

Workup

  1. stirringstirred for 4 hours while the bath temperature
  2. temperaturegradually warmed up
  3. stirringthe reaction was stirred overnight while the reaction
  4. temperaturewas warmed up to room temperature
  5. customThe solvent was mostly removed via vacuum
  6. customthe crude was partitioned between ethyl acetate and water
  7. customThe ethyl acetate layer was separated
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe product was obtained by flash column
  12. washeluted with ether in hexane from 0 to 30% (3.9 g, 74% yield)

Sources & evidence

ORD record
ord-874a9661da6f44589b3b56e8f7a06212
Source dataset
uspto-grants-2011_10
Patent number
US08044043B2

Reaction notes

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