Benzyl Bromide → 1-benzyl-1H-imidazole-2-carbaldehyde

HRID 908037

Reaktionsgleichung

Reaktionsgleichung von HRID 908037
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH2:15]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 249551H-imidazole-2-carbaldehyde

Produkt 1

HCID 1390821-benzyl-1H-imidazole-2-carbaldehydeAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 1H-imidazole-2-carbaldehyde (240 mg, 2.4 mmol) and potassium carbonate (662 mg, 4.8 mmol) in acetonitrile (5 mL) at 0° C. was added dropwise (bromomethyl)benzene (493 mg, 2.88 mmol). The mixture was stirred at 40° C. for 4 hr. Then the mixture was filtrated, evaporated to remove the acetonitrile from the filtrate, added EtOAc to extract the residues, and washed the extract with brine and water. The organic layer was dried with anhydrous Na2SO4, concentrated, and chromatographed on a silica gel column (EtOAc:hexane=1:9) to obtain the title compound (430 mg, yield 95%). LC-MS (ESI) m/z: 187 (M+1)+.

Aufarbeitung

  1. filtrationThen the mixture was filtrated
  2. customevaporated
  3. customto remove the acetonitrile from the filtrate
  4. additionadded EtOAc
  5. extractionto extract the residues
  6. washwashed the
  7. extractionextract with brine and water
  8. dry with materialThe organic layer was dried with anhydrous Na2SO4
  9. concentrationconcentrated
  10. customchromatographed on a silica gel column (EtOAc:hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-96af5264065d4c51bae7604ec49976ea
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012976B2

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