1,1,1,3,3,3-Hexafluoropropan-2-yl 2,3,5,6-tetrafluoro-4-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzoate Full article
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MolBank
ISSN: 1422-8599 |
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| Output data | Year: 2025, Volume: 2025, Number: 3, Article number : M2063, Pages count : DOI: 10.3390/M2063 | ||||
| Tags | acyl chloride alcoholysis; hexafluoro-2-propanol; pentafluorobenzoyl chloride; side reaction | ||||
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Funding (1)
| 1 | Российский Научный Фонд | 25-23-00445 |
Abstract:
Acyl chloride alcoholysis is a fundamental and typically high-yielding method for ester synthesis. However, competitive side reactions can occur when the acyl chloride possesses multiple electrophilic sites and the alcohol is a strong nucleophile. We report an example of this phenomenon: the reaction of pentafluorobenzoyl chloride with 1,1,1,3,3,3-hexafluoropropan-2-ol yields not only the expected ester but also a significant quantity of the 1,1,1,3,3,3-hexafluoropropan-2-yl 2,3,5,6-tetrafluoro-4-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzoate. The formation of the latter results from an effective nucleophilic aromatic substitution (SNAr) at the para-fluorine position of the pentafluorophenyl ring by the hexafluoroisopropoxide anion.
Cite:
Kascheeva S.S.
, Lastovka A.V.
, Vinogradov A.S.
, Parkhomenko D.A.
1,1,1,3,3,3-Hexafluoropropan-2-yl 2,3,5,6-tetrafluoro-4-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzoate
MolBank. 2025. V.2025. N3. M2063 . DOI: 10.3390/M2063 WOS
1,1,1,3,3,3-Hexafluoropropan-2-yl 2,3,5,6-tetrafluoro-4-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzoate
MolBank. 2025. V.2025. N3. M2063 . DOI: 10.3390/M2063 WOS
Dates:
| Submitted: | Aug 20, 2025 |
| Accepted: | Sep 15, 2025 |
| Published online: | Sep 18, 2025 |
Identifiers:
| Web of science: | WOS:001580311900001 |
Citing:
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