3-Acetylbenzothiophene → 1-(1-Benzothiophen-3-yl)-2-bromoethan-1-one

HRID 362254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362254
[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:37]1[C:38]2[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=2[S:40][CH:41]=1)(=[O:36])[CH3:35]>O1CCCC1>[Br:1][CH2:35][C:34]([C:37]1[C:38]2[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=2[S:40][CH:41]=1)=[O:36]

Komponenten

4

Edukt 2

HCID 143163-AcetylbenzothiopheneHCID 17977687Phenyltrimethylammonium bromide dibromide

Produkt 1

HCID 27763411-(1-Benzothiophen-3-yl)-2-bromoethan-1-oneAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Phenyltrimethylammonium tribromide (26.32 g) was added in portions over 45 minutes at -5° C. under nitrogen to a stirred solution of 3-acetylbenzo[b]thiophen (12.34 g) in tetrahydrofuran (100 ml), then the mixture was stirred at ambient temperature for 1 hour. The resulting solid was collected by filtration, washed with ether (100 ml), dried in vacuo at ambient temperature, and crystallised from ethanol to give 3-(2-bromoacetyl)benzo[b]thiophen as a white solid (10.9 g).

Aufarbeitung

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with ether (100 ml)
  3. customdried in vacuo at ambient temperature
  4. customcrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0e71f0129730448488e796e0805809e6
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869492

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