Solvent-free nitration of electron-rich arenes

Bhumasamudram Jagadish; Nathaniel R. Hurley; Eugene A. Mash

doi:10.1080/00397911.2017.1378682

Solvent-free nitration of electron-rich arenes

Bhumasamudram Jagadish, Nathaniel R. Hurley, Eugene A. Mash

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

Abstract

Nitration of relatively electron-rich arenes does not require an additive or a solvent. For example, reaction on a gram scale of anisole with acetyl nitrate, generated in situ by mixing 100% HNO₃ with acetic anhydride, produced 2,4-dinitroanisole in 82% yield after crystallization of the crude product. Results with five additional monosubstituted benzene derivatives possessing highly activated, weakly activated, or weakly deactivated rings are reported.

Original language	English (US)
Pages (from-to)	2395-2398
Number of pages	4
Journal	Synthetic Communications
Volume	47
Issue number	24
DOIs	https://doi.org/10.1080/00397911.2017.1378682
State	Published - Dec 17 2017
Externally published	Yes

Keywords

2,4-Dinitroanisole
additive-free
nitration
solvent-free

ASJC Scopus subject areas

Organic Chemistry

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10.1080/00397911.2017.1378682

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title = "Solvent-free nitration of electron-rich arenes",

abstract = "Nitration of relatively electron-rich arenes does not require an additive or a solvent. For example, reaction on a gram scale of anisole with acetyl nitrate, generated in situ by mixing 100% HNO3 with acetic anhydride, produced 2,4-dinitroanisole in 82% yield after crystallization of the crude product. Results with five additional monosubstituted benzene derivatives possessing highly activated, weakly activated, or weakly deactivated rings are reported.",

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author = "Bhumasamudram Jagadish and Hurley, {Nathaniel R.} and Mash, {Eugene A.}",

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AU - Hurley, Nathaniel R.

AU - Mash, Eugene A.

PY - 2017/12/17

Y1 - 2017/12/17

N2 - Nitration of relatively electron-rich arenes does not require an additive or a solvent. For example, reaction on a gram scale of anisole with acetyl nitrate, generated in situ by mixing 100% HNO3 with acetic anhydride, produced 2,4-dinitroanisole in 82% yield after crystallization of the crude product. Results with five additional monosubstituted benzene derivatives possessing highly activated, weakly activated, or weakly deactivated rings are reported.

AB - Nitration of relatively electron-rich arenes does not require an additive or a solvent. For example, reaction on a gram scale of anisole with acetyl nitrate, generated in situ by mixing 100% HNO3 with acetic anhydride, produced 2,4-dinitroanisole in 82% yield after crystallization of the crude product. Results with five additional monosubstituted benzene derivatives possessing highly activated, weakly activated, or weakly deactivated rings are reported.

KW - 2,4-Dinitroanisole

KW - additive-free

KW - nitration

KW - solvent-free

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JF - Synthetic Communications

IS - 24

ER -

Solvent-free nitration of electron-rich arenes

Abstract

Keywords

ASJC Scopus subject areas

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