Acetic Anhydride → N-(4-Bromo-2-methylphenyl)acetamide

HRID 2216249

Reaktionsgleichung

Reaktionsgleichung von HRID 2216249
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:16][C:11]1[CH:10]=[C:9]([Br:8])[CH:15]=[CH:14][C:12]=1[NH:13][C:5]([CH3:6])=[O:7]

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 114234-Bromo-2-methylanilineHCID 517045Sodium Acetate

Produkt 1

HCID 222277N-(4-Bromo-2-methylphenyl)acetamideAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Acetic anhydride (15.2 ml, 0.16 mol) was added dropwise to a stirred mixture of 4-bromo-2-methylaniline (10.0 g, 0.054 mol) and sodium acetate (2.52 g, 0.056 mol) in toluene (150 ml). Once the addition was complete the mixture was warmed to 85° C. and stirred for 40 minutes. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with water. The organic solution was evaporated in vacuo, a further quantity of toluene was added and then the solvent was evaporated to give 4-bromo-2-methylacetanilide (12.3 g), as a colourless solid.

Aufarbeitung

  1. additionOnce the addition
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water
  4. customThe organic solution was evaporated in vacuo
  5. additiona further quantity of toluene was added
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-469f6efd7aa8437e88791e175f260172
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112553B1

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