2-Chlorothiophene → Methanone, (5-chloro-2-thienyl)phenyl-

HRID 1707724

Reaktionsgleichung

Reaktionsgleichung von HRID 1707724
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>>[C:1]([C:13]1[S:12][C:11]([Cl:10])=[CH:15][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([C:13]1[S:12][C:11]([O:26][C:23]2[CH:24]=[CH:25][C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:21][CH:22]=2)=[CH:15][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 72992-ChlorothiopheneHCID 73934-tert-ButylphenolHCID 7412Benzoyl chloride

Produkt 2

HCID 901505Methanone, (5-chloro-2-thienyl)phenyl-HCID 199353132-Benzoyl-5-(4-t-butyl-phenoxy)thiophene

Versuchsvorschrift

2-benzoyl-5-chlorothiophene was synthesized via Friedel-Crafts acylation of benzoyl chloride with 2-chlorothiophene. This was reacted under standard conditions with 4-t-butyl phenol to produce 2-benzoyl-5-(4-t-butyl-phenoxy)thiophene. It was discovered by thin layer chromatography that the displacement of the acyl chlorine proceeds completely with no side reactions. Complete nucleophilic displacement demonstrates that this reaction meets the requirements necessary for high polymer formation via a step growth reaction.

Quellen und Nachweise

ORD-Eintrag
ord-c7ebfff87e6041958baf6f44204345a9
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05354836

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