Phosphorus oxychloride → 4-Chloro-2,6-bis(trifluoromethyl)quinoline

HRID 1791951Notes

Reaction equation

O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 1785161332,6-Bis(trifluoromethyl)quinolin-4(1H)-one

Product 1

HCID 6270374-Chloro-2,6-bis(trifluoromethyl)quinoline

Procedure

4-Hydroxy-2,6-bis(trifluoromethyl)quinoline (1.28 g) was dissolved in phosphorus oxychloride (5.0 mL), and the mixture was stirred at room temperature for 17 hr. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture was extracted with chloroform and concentrated under reduced pressure to give 4-chloro-2,6-bis(trifluoromethyl)quinoline (1.17 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution
additionwas added to the residue
extractionThe mixture was extracted with chloroform
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-aaeb23c7d47e4c37afe76145535b2e03
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074794B2

Reaction notes

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