3-Bromobenzaldehyde → 2-(3-Bromophenyl)-4,5-dimethyloxazole-3-oxide

HRID 2228979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2228979
[CH3:1][C:2](=[N:6][OH:7])[C:3](=[O:5])[CH3:4].[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O>C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([C:12]2[O:5][C:3]([CH3:4])=[C:2]([CH3:1])[N+:6]=2[O-:7])[CH:14]=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 765833-BromobenzaldehydeHCID 63989692-Oxime 2,3-butanedione

Produkt 1

HCID 40877752-(3-Bromophenyl)-4,5-dimethyloxazole-3-oxideAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 2,3-butanedione monooxime (50 g, 0.49 mol) and 3-bromobenzaldehyde (101 g, 0.54 mol) in acetic acid (500 mL) was cooled to 0° C. and then gaseous HCl was bubbled through the solution for 35 min while the reaction was stirred in an ice bath. Diethyl ether (500 mL) was then added to the reaction to precipitate the product and the resultant slurry stirred 45 min at 0° C. before being filtered. The solids were rinsed with Et2O (50 mL), taken up in water (1 L) and concentrated NH4OH (60 mL) added to the slurry. This mixture was extracted with CHCl3, the organic layer was dried (MgSO4), and the solvent removed in vacuo to give 97.4 g (74%) of 2-(3-bromophenyl)-4,5-dimethyloxazole-3-oxide as a white solid. The compound should be used directly with 24-48 h. 1H NMR (300 MHz, CDCl3) δ8.60 (s, 1H), 8.40 (d, J=8.0 Hz, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 2.39 (s, 3H), 2.20 (s, 3H).

Aufarbeitung

  1. customgaseous HCl was bubbled through the solution for 35 min while the reaction
  2. additionDiethyl ether (500 mL) was then added to the reaction
  3. customto precipitate the product
  4. stirringthe resultant slurry stirred 45 min at 0° C.
  5. filtrationbefore being filtered
  6. washThe solids were rinsed with Et2O (50 mL)
  7. additionconcentrated NH4OH (60 mL) added to the slurry
  8. extractionThis mixture was extracted with CHCl3
  9. dry with materialthe organic layer was dried (MgSO4)
  10. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d073ceb61808435e9455979324412d45
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06417212B1

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