Phosphorus oxychloride → 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine

HRID 2403634Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:7](=O)[NH:8][CH:9]=1)([O-:3])=[O:2].O=P(Cl)(Cl)[Cl:17].P(Cl)(Cl)(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>>[Cl:17][C:7]1[C:6]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1

Participants

Reactant 4

HCID 24813Phosphorus oxychloride

HCID 24819Phosphorus pentachloride

HCID 516892Sodium Bicarbonate

HCID 27750952-Hydroxy-5-nitro-3-(trifluoromethyl)pyridine

Product 1

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Conditions

Temperature: 115 °C

Procedure

A mixture of 5-nitro-3-(trifluoromethyl)pyridin-2(1H)-one 3 (1.50 g, 7.21 mmol), POCl3 (2.76 g, 18.02 mmol) and PCl5 (1.4 g, 10.09 mmol) is heated to about 110-120° C. for 8 hours and then poured into ice water. The mixture is neutralized with solid NaHCO3 and extracted with ethyl acetate (3×40 ml). The combined organic phases is dried over Na2SO4 and all solvents removed under reduced pressure to obtain 2-chloro-5-nitro-3-(trifluoromethyl)pyridine 4.

Workup

extractionextracted with ethyl acetate (3×40 ml)
dry with materialThe combined organic phases is dried over Na2SO4
customall solvents removed under reduced pressure

Sources & evidence

ORD record: ord-9be85fd697204acbab0e7ea97ed046d5
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802689B2

Reaction notes

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