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Phenyltrimethylammonium bromide dibromide → HCID 22473879, Verbindung

HRID 2183637
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2183637
[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.[CH3:34][C:35]1[C:43]2[CH:42]=[C:41]([C:44](=[O:47])[CH2:45][CH3:46])[S:40][C:39]=2[CH:38]=[CH:37][CH:36]=1>O1CCCC1>[Br:1][CH:45]([CH3:46])[C:44]([C:41]1[S:40][C:39]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:34])[C:43]=2[CH:42]=1)=[O:47]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 17977687Phenyltrimethylammonium bromide dibromide2×HCID 22473751HCID 22473751, Verbindung

Produkt 1

HCID 22473879HCID 22473879, VerbindungAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Phenyltrimethylammonium tribromide (1.47 g) was added in portions under nitrogen at 0° C. over 10 minutes to a stirred solution of 1-(4-methylbenzo[b]thiophen-2-yl)propan-1-one (0.53 g) in tetrahydrofuran (15 ml), then the mixture was stirred at 0° C. for 3 hours and at ambient temperature for 16 hours. Further phenyltrimethylammonium tribromide (0.49 g) was added, then the mixture was stirred at ambient temperature for 26 hours and filtered. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica using a 4:1 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 2-bromo-1-(4-methylbenzo[b]thiophen-2-yl)propan-1-one (0.3 g) as a yellow solid which was used without further purification.

Aufarbeitung

  1. stirringthe mixture was stirred at ambient temperature for 26 hours
  2. filtrationfiltered
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography over silica using
  5. additiona 4:1 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane as eluant
  6. customthe solvents removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-14686ca1372f4bce820308c7a14cba23
Quelldatensatz
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06900216B2

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