Benzyl Bromide → N,N-Dibenzyl-3-bromoaniline

HRID 5296

Reaktionsgleichung

Reaktionsgleichung von HRID 5296
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[O-2].[Mg+2].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[CH2:11]([N:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Br:1])[CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 115623-BromoanilineHCID 6850729Magnesium monoxide

Produkt 1

HCID 18692655N,N-Dibenzyl-3-bromoanilineAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 16 g of 3-bromoaniline, 15 g magnesium oxide and 31.8 g benzylbromide in 100 mL dry dimethylformamide was stirred for 47 hours at room temperature, under nitrogen. The precipitated magnesium salts were filtered. The filtrate was diluted with water and extracted with ether. The ether extracts were combined, washed with water and dried over anhydrous sodium sulfate. The sodium sulfate was filtered and the ether evaporated in vacuo to give a brownish solid. The brownish solid was recrystallized from isopropanol to yield 20.75 g of N,N-dibenzyl-3-bromoaniline as a white solid. The structure was confirmed by NMR.

Aufarbeitung

  1. filtrationThe precipitated magnesium salts were filtered
  2. additionThe filtrate was diluted with water
  3. extractionextracted with ether
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe sodium sulfate was filtered
  7. customthe ether evaporated in vacuo
  8. customto give a brownish solid
  9. customThe brownish solid was recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-be1ccb7d1f2e45ccb333bd9c40dea672
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244771

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