Allyl bromide → 1-allyl-2-bromo-1H-benzo[d]imidazole

HRID 1051729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051729
[Br:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[CH2:11](Br)[CH:12]=[CH2:13].O1CCOCC1.[OH-].[Na+]>C(OCC)(=O)C>[CH2:13]([N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[Br:1])[CH:12]=[CH2:11]

Komponenten

6

Edukt 4

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 27762812-Bromobenzimidazole

Produkt 1

HCID 1180762101-allyl-2-bromo-1H-benzo[d]imidazoleAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-bromo-1H-benzo[d]imidazole (0.400 g, 2.04 mmol), allyl bromide (0.35 mL, 4.08 mmol), 1,4-dioxane (15 mL), and 2 M aqueous sodium hydroxide solution (15 mL, 3.00 mmol) stirred for 2 h at 100° C. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 mL). The organic phase was separated and washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via preparative thin layer chromatography (eluting with 20% ethyl acetate/petroleum ether) to afford 1-allyl-2-bromo-1H-benzo[d]imidazole (0.251 g, 52%) as a yellow oil. MS (ESI, pos. ion) m/z 237, 239 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic phase was separated
  3. washwashed with brine (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified via preparative thin layer chromatography (eluting with 20% ethyl acetate/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-7205731dc75748158df4228c83848a72
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388161B2

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