Butyl bromide → N-butyl-N-acetyl-2,4-difluoroaniline

HRID 1494446

Reaktionsgleichung

Reaktionsgleichung von HRID 1494446
[CH2:1](Br)[CH2:2][CH2:3][CH3:4].[OH-].[K+].[C:8]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19])(=[O:10])[CH3:9]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O.C1(C)C=CC=CC=1>[CH2:1]([N:11]([C:8](=[O:10])[CH3:9])[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19])[CH2:2][CH2:3][CH3:4]

Komponenten

7

Edukt 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 96093Acetamide, N-(2,4-difluorophenyl)-

Produkt 1

HCID 19827549N-butyl-N-acetyl-2,4-difluoroanilineAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

0.9 g of triethylbenzylammonium chloride, 6.9 g of butyl bromide and a solution of 5.7 g of KOH in 6 ml of water are added to a stirred solution of 3.4 g of N-acetyl-2,4-difluoroaniline (Example 2) in 60 ml of toluene. The emulsion produced is warmed at 97° (reflux). After 1 h, the emulsion is cooled to room temperature and diluted with 20 ml of water. The two phases are separated, and the organic phase is dried over MgSO4 and evaporated in vacuo. The liquid crude product is purified by medium-pressure chromatography. 3.1 g of N-butyl-N-acetyl-2,4-difluoroaniline are obtained as a brownish oil.

Aufarbeitung

  1. customThe emulsion produced
  2. temperatureis warmed at 97°
  3. temperature(reflux)
  4. customThe two phases are separated
  5. dry with materialthe organic phase is dried over MgSO4
  6. customevaporated in vacuo
  7. customThe liquid crude product is purified by medium-pressure chromatography

Quellen und Nachweise

ORD-Eintrag
ord-97ddca6efec049b8af0e4bcb966496bc
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05026625

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