Water → 3-(Trifluoromethyl)quinoline

HRID 1519823Notes

Reaction equation

HRID 1519823 reaction equation
I[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F-:12].[K+].Cl[C:15]([F:21])([F:20])C(OC)=O.O>CN(C)C=O.C(OCC)(=O)C>[F:20][C:15]([F:21])([F:12])[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 962WaterHCID 73935Methyl chlorodifluoroacetateHCID 522689Potassium FluorideHCID 112538363-Iodoquinoline

Product 1

HCID 120251663-(Trifluoromethyl)quinolineYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Iodoquinoline (13.65 g, 53.5 mmol), cuprous iodide (21.12, 111 mmol), potassium fluoride (7.11 g, 122 mmol), and methyl 2-chloro-2,2-difluoroacetate (23 ml, 216 mmol) in dimethylforamide (200 ml) was placed into a preheated oil bath at 120° C. After stirring for 6 h, the solution was diluted water and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with 99:1, 49:1, 24:1, 23:2, 9:1, and 4:1 hexane:ethyl acetate as the eluant to afford 3.89 g (37% yield) of 3-(trifluoromethyl)quinoline. Method [7] retention time 4.67 min by HPLC (M+ 198).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 99:1, 49:1, 24:1, 23:2, 9:1, and 4:1 hexane

Sources & evidence

ORD record
ord-1a8322b899244cdf82fc810178e45aa2
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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