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

Standard

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. / Kascheeva, Sofia S.; Lastovka, Anastasiya V.; Vinogradov, Andrey S. et al.

In: MolBank, Vol. 2025, No. 3, M2063, 18.09.2025.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{18969380471d45da8552656bd7bebf4c,

title = "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",

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.",

keywords = "acyl chloride alcoholysis, hexafluoro-2-propanol, pentafluorobenzoyl chloride, side reaction",

author = "Kascheeva, {Sofia S.} and Lastovka, {Anastasiya V.} and Vinogradov, {Andrey S.} and Parkhomenko, {Dmitriy A.}",

note = "This research was funded by Russian Science Foundation, grant number 25-23-00445, https://rscf.ru/project/25-23-00445/ (accessed on 14 September 2025). ",

year = "2025",

month = sep,

day = "18",

doi = "10.3390/M2063",

language = "English",

volume = "2025",

journal = "MolBank",

issn = "1422-8599",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "3",

}

RIS

TY - JOUR

T1 - 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

AU - Kascheeva, Sofia S.

AU - Lastovka, Anastasiya V.

AU - Vinogradov, Andrey S.

AU - Parkhomenko, Dmitriy A.

N1 - This research was funded by Russian Science Foundation, grant number 25-23-00445, https://rscf.ru/project/25-23-00445/ (accessed on 14 September 2025).

PY - 2025/9/18

Y1 - 2025/9/18

N2 - 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.

AB - 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.

KW - acyl chloride alcoholysis

KW - hexafluoro-2-propanol

KW - pentafluorobenzoyl chloride

KW - side reaction

UR - https://www.mendeley.com/catalogue/3e3a89cd-8581-396e-8566-7c210104415e/

UR - https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=105017811679&origin=inward

U2 - 10.3390/M2063

DO - 10.3390/M2063

M3 - Article

VL - 2025

JO - MolBank

JF - MolBank

SN - 1422-8599

IS - 3

M1 - M2063

ER -

ID: 70629633