20885-12-5

Usage

Synthesis

However, a recent study demonstrated that a range of substituted pyridines reacted with fluorine diluted with nitrogen giving 2-fluoropyridine derivatives in acceptable yields. Thus, 2-chloropyridine gave mostly 2-chloro-6-fluoropyridine.

Chemical Properties

Light yellow needles

InChI:InChI=1/C5H3ClFN/c6-4-2-1-3-5(7)8-4/h1-3H

Upstream product

• 109-09-1 2-chloropyridine 
• 119071-51-1 C₅H₄ClFN⁽¹⁺⁾*BF₄^(1-) 

Downstream Products

• 1095223-59-8 1-(6-chloro-2-fluoro-pyridin-3-yl)-2-(3,4-dichloro-phenoxy)-ethanone 
• 1095223-57-6 1-(6-chloro-2-fluoro-pyridin-3-yl)-2-(4-chloro-phenoxy)-ethanone 
• 1095223-55-4 1-(6-chloro-2-fluoro-pyridin-3-yl)-2-phenoxy-ethanone 
• 1095223-51-0 2-benzyloxy-1-(6-chloro-2-fluoro-pyridin-3-yl)-ethanone 
• 1095223-53-2 1-(6-chloro-2-fluoro-pyridin-3-yl)-2-(4-methoxy-phenoxy)-ethanone 
• 869109-01-3 Methyl 4-(6-fluoropyridin-2-yloxy)benzenecarboxylate 
• 1227509-94-5 6-chloro-2-fluoro-3-pyridinemethanol 
• 1227577-88-9 6-chloro-3-(chloromethyl)-2-fluoropyridine 
• 1093880-37-5 6-chloro-2-fluoropyridine-3-carboxaldehyde 
• 1060801-42-4 6-chloro-N,N-dimethylpyridin-2-amine 
• 1146615-89-5 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 80364-46-1 N-(6-chloropyridin-2-yl)acetamide 
• 1380584-11-1 (+)-phantasmidine Mosher's amide 
• 1380601-17-1 phantasmidine Mosher's amide 

Relevant academic research and scientific papers

Elemental fluorine. Part 10.1 Selective fluorination of pyridine, quinoline and quinoxaline derivatives with fluorine-iodine mixtures

Selective fluorination of a range of pyridine and quinoline substrates to give corresponding 2-fluoro-derivatives can be readily achieved in high yield at room temperature using elemental fluorine-iodine mixtures. Reaction of fluorine with iodine forms, in situ, systems that function like sources of both iodonium and fluoride ions and fluorination of heterocyclic derivatives is suggested to proceed by fluoride ion attack on intermediate W-iodo-heterocyclic species. Quinoxaline derivatives react under similar conditions to give either the 2-fluoro- or 2,3-difluoro-quinoxaline derivatives depending on the ratio of fluorine passed through the solution. In related processes, pyridine can be alkoxylated upon reaction of an appropriate alcohol and fluorine.

Preparation of 2-Fluoropyridines via Base-Induced Decomposition of N-Fluoropyridinium Salts

N-Fluoropyridinium salts with either BF4-, SbF6-, or PF6- as a counteranion were treated with excess base such as triethylamine at room temperature to give 2-fluoropyridine in good yield.This method was succesfully applied to the preparation of 2-fluoropyridine derivatives possessing electron-donating or -withdrawing substituents using substituted N-fluoropyridinium tetrafluoroborates.Pyridine-F2 compounds produced through reactions of pyridines with molecular fluorine were also treated with base to give 2-fluoropyridines but in low yields.These reactions are considered to occur through a carbene mechanism as follows: a novel N-F-containing cyclic carbene (3), generated from the N-fluoropyridinium salts by 2-proton abstraction, reacts with fluorine atoms from counteranions such as BF4-, SbF6-, or PF6-, followed by elimination of F- from the N-F moiety, to yield 2-fluoropyridines.Previously reported findings in reactions of pyridines with molecular fluorine are explained on the basis of this mechanism.

DIRECT FLUORINATION OF SUBSTITUTED PYRIDINES

The direct fluorination of pyridines bearing alkyl, halogen, ester, or ketone functions has been employed to prepare the corresponding 2-fluoro-substituted pyridines.