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

HRID 1829160Notes

Reaction equation

HRID 1829160 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

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 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

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

Sources & evidence

ORD record
ord-405f0cdc792644d7a54e865f02a624b8
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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