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

HRID 562889Notes

Reaction equation

HRID 562889 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

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 70297m-Chloroperbenzoic acidHCID 46311148Methyl 3-fluoropyridine-4-carboxylate

Product 2

HCID 24820381Methyl 2-chloro-3-fluoropyridine-4-carboxylateHCID 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).

Workup

  1. customThe product was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-74914df1a6a04126a214f87be0ed016d
Source dataset
uspto-grants-2011_11
Patent number
US08067446B2

Reaction notes

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