Utilizing Acetyl Hypofluorite for Chlorination, Bromination, and Etherification of the Pyridine System

David Hebel, Shlomo Rozen

Research output: Contribution to journalArticlepeer-review

Abstract

Acetyl hypofluorite, which is easily made from F2, possesses a strong electrophilic fluorine. This electrophile is able to attach itself to the nitrogen atom of pyridine and activate the ring toward nucleophilic attacks. The ultimate elimination of HF results in an overall easy nucleophilic displacement of the hydrogen of the important 2-position. The nucleophiles used; Clδ-, Brδ-, and ROδ-, originate from solvents such as CH2Cl2, CH2Br2, and various primary alcohols. Thus, 2-halo- or 2-alkoxypyridines were formed. The reaction conditions (room temperature, very short reaction times, and good yields) transform the task of direct substitution of the pyridine ring from an extremely difficult to a very easy procedure.

Original languageEnglish
Pages (from-to)6298-6301
Number of pages4
JournalJournal of Organic Chemistry
Volume56
Issue number22
DOIs
StatePublished - 1 Oct 1991

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