3-Bromobenzyl bromide → 1-Bromo-3-(but-3-en-1-yl)benzene

HRID 921207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921207
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:12][CH:11]=[CH2:10])[CH:3]=1

Komponenten

4

Edukt 2

HCID 699793-Bromobenzyl bromideHCID 178455850HCID 178455850, Verbindung

Produkt 1

HCID 157251651-Bromo-3-(but-3-en-1-yl)benzeneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-3-(bromomethyl)benzene (1 g, 4.00 mmol) in THF (15 mL) was added allylmagnesium bromide (4.80 mL, 4.80 mmol) and stirred at rt for 1 h, then refluxed for 2 h. It was then quenched with NH4Cl, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil. It was then purified by 5% EtOAc/hexane to isolate 1-bromo-3-(but-3-en-1-yl)benzene (0.7 g, 3.32 mmol, 83% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.41-7.31 (m, 2H), 7.21-7.12 (m, 2H), 5.85 (ddt, J=17.1, 10.3, 6.6 Hz, 1H), 5.14-4.94 (m, 2H), 2.75-2.64 (m, 2H), 2.45-2.31 (m, 2H).

Aufarbeitung

  1. temperaturerefluxed for 2 h
  2. customIt was then quenched with NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain an oil
  8. customIt was then purified by 5% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e1b2300de3c445f3b3b0e10b03029053
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273067B2

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