Phenyltrimethylammonium bromide dibromide → 5-(Bromoacetyl)-2,3-dimethoxybenzonitrile

HRID 274504

Reaktionsgleichung

Reaktionsgleichung von HRID 274504
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[C:34]([C:36]1[C:37]([O:47][CH3:48])=[C:38]([O:45][CH3:46])[CH:39]=[C:40]([C:42](=[O:44])[CH3:43])[CH:41]=1)#[N:35]>O1CCCC1>[Br:1][CH2:43][C:42]([C:40]1[CH:39]=[C:38]([O:45][CH3:46])[C:37]([O:47][CH3:48])=[C:36]([CH:41]=1)[C:34]#[N:35])=[O:44]

Komponenten

4

Edukt 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 214589805-Acetyl-2,3-dimethoxybenzonitrile

Produkt 1

HCID 214589615-(Bromoacetyl)-2,3-dimethoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3.48 g of phenyltrimethylammonium bromide dibromide dissolved in 30 ml of tetrahydrofuran are added dropwise at room temperature within 45 minutes to 1.9 g of 5'-cyano-3',4'-dimethoxyacetophenone dissolved in 30 ml of tetrahydrofuran, whereupon the mixture is stirred for 30 minutes. Thereupon, the reaction mixture is poured into 120 ml of ice-water and extracted three times with 70 ml of methylene chloride. The combined methylene chloride phases are washed with 2N sulfuric acid, dried over sodium sulfate and evaporated. The residue is chromatographed on 20 g of silica gel with methylene chloride. After recrystallization from methylene chloride/hexane there is obtained 5-(bromoacetyl)-2,3-dimethoxybenzonitrile of m.p. 138°-141°.

Aufarbeitung

  1. extractionextracted three times with 70 ml of methylene chloride
  2. washThe combined methylene chloride phases are washed with 2N sulfuric acid
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on 20 g of silica gel with methylene chloride
  6. customAfter recrystallization from methylene chloride/hexane there

Quellen und Nachweise

ORD-Eintrag
ord-b3cc1b0546764212b05282def5180ba2
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389653

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