Potassium Carbonate → 5-(4-Bromophenyl)-1,3-oxazole

HRID 1063892

Reaktionsgleichung

Reaktionsgleichung von HRID 1063892
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C1(C)C=CC(S([CH2:19][N+:20]#[C-:21])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[O:7][CH:21]=[N:20][CH:19]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 161915Tosylmethyl isocyanide

Produkt 1

HCID 27764185-(4-Bromophenyl)-1,3-oxazoleAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-bromobenzaldehyde (5.00 g), p-toluenesulfonylmethyl isocyanide (5.43 g) and potassium carbonate (5.60 g) in methanol (50 ml) was heated under reflux for 2 hours. After evaporation of solvent, ethyl acetate and saturated ammonium chloride solution were added. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (2:1) to give 5-(4-bromophenyl)oxazole as a pale yellow powder (5.77 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of solvent, ethyl acetate and saturated ammonium chloride solution
  4. additionwere added
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography
  10. washeluting with a mixture of hexane and ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-0ff63b8c6a96497ab74f9906123bf40e
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967197B2

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