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Fluorination and chlorination of nitroalkyl groups

Lookup NU author(s): Philip Butler, Emeritus Professor Bernard Golding, Dr Gilles Laval, Dr Hosein Loghmani-Khouzani, Professor Majid Sadeghi

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Abstract

Heterocycles substituted with a nitromethyl (CH2NO2) or phenyl-nitromethyl (CHPhNO2) group were prepared by reaction of a methyl- or phenylmethyl-substituted heterocycle, respectively, with lithium di-isopropylamide followed by quenching the intermediate carbanion with methyl nitrate. Conversion of CH2NO2 attached to an alkyl or aryl moiety into a dichloronitromethyl (CCl2NO2) group was achieved using N-chlorosuccinimide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane. Similarly, CH2NO2 attached to an alkyl or aryl group was converted into difluoronitromethyl (CF2NO2) using either 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™) or N-fluorobenzenesulfonimide with DBU as base and dichloromethane as solvent. Reaction of ω-nitroacetophenone with Selectfluor/DBU in dimethylformamide followed by acidification and distillation gave the parent difluoronitromethane in a useful 'one-pot' procedure. © 2007 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Butler P, Golding BT, Laval G, Loghmani-Khouzani H, Ranjbar-Karimi R, Sadeghi MM

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2007

Volume: 63

Issue: 45

Pages: 11160-11166

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/j.tet.2007.08.020

DOI: 10.1016/j.tet.2007.08.020

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