Phosphorus oxychloride → Methyl 2-chloro-3-fluoropyridine-4-carboxylate

Reaction equation

[F:1][C:2]1[CH:11]=[N:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:12]C1C=CC=C(C(OO)=O)C=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:12][C:9]1[CH:8]=[C:3]([C:2]([F:1])=[CH:11][N:10]=1)[C:4]([O:6][CH3:7])=[O:5].[Cl:25][C:11]1[C:2]([F:1])=[C:3]([CH:8]=[CH:9][N:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 70297m-Chloroperbenzoic acid

HCID 46311148Methyl 3-fluoropyridine-4-carboxylate

Product 2

HCID 24820381Methyl 2-chloro-3-fluoropyridine-4-carboxylate

HCID 46311230Methyl 2-chloro-5-fluoropyridine-4-carboxylate

Procedure

Methyl 3-fluoroisonicotinate was oxidized with 3-chloroperbenzoic acid, followed by heating in the presence of phosphoryl chloride. The product was separated by silica gel column chromatography to obtain methyl 2-chloro-5-fluoroisonicotinate (EI: 189) and methyl 2-chloro-3-fluoroisonicotinate (EI: 189).