2-Bromobenzyl bromide → 2-(But-3-en-1-yl)bromobenzene

HRID 1827293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827293
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][CH2:12][CH:11]=[CH2:10]

Komponenten

4

Edukt 2

HCID 769652-Bromobenzyl bromideHCID 178455850HCID 178455850, Verbindung

Produkt 1

HCID 34857122-(But-3-en-1-yl)bromobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice cold solution of 2-bromobenzyl bromide (5.00 g, 0.020 mol) in THF (25 mL) was added 1M allyl magnesium bromide (100 mL, 0.100 mol) slowly via cannula. The reaction mixture was stirred at reflux for 1.5 h, cooled in an ice bath and quenched with 50 mL of aqueous 2M H2SO4. Water (50 mL) was added to dissolve any remaining solid and the layers were separated. The aqueous layer was extracted with Et2O (2×150 mL). The combined organic extracts Were dried over Na2SO4, filtered and concentrated to yield 1-bromo-2-but-3-enyl-benzene as a light yellow oil. The isolated crude product was carried forward without further purification.

Aufarbeitung

  1. temperatureat reflux for 1.5 h
  2. temperaturecooled in an ice bath
  3. customquenched with 50 mL of aqueous 2M H2SO4
  4. additionWater (50 mL) was added
  5. dissolutionto dissolve any remaining solid
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with Et2O (2×150 mL)
  8. dry with materialThe combined organic extracts Were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ed0ffa8b47004e11a7fec2e6b4636536
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053101B2

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