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

HRID 1707724

Reaction equation

HRID 1707724 reaction equation
[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

Participants

5

Reactant 3

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

Product 2

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

Procedure

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.

Sources & evidence

ORD record
ord-c7ebfff87e6041958baf6f44204345a9
Source dataset
uspto-grants-1994_10
Patent number
US05354836

Linked notes

Loading…