Ethylene Glycol → 3-(2-Trifluoromethyl-phenylsulfanyl)-quinoline

HRID 2063932Notes

Reaction equation

HRID 2063932 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][C:13]([F:22])([F:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[SH:20].C(O)CO.C([O-])([O-])=O.[K+].[K+]>C(O)(C)C.[Cu]I>[F:22][C:13]([F:12])([F:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][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 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 27778892-(Trifluoromethyl)benzenethiolHCID 112538363-Iodoquinoline

Product 1

HCID 532316873-(2-Trifluoromethyl-phenylsulfanyl)-quinolineYield 112.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 3-iodoquinoline (6 g, 23.5 mmol), 2-trifluoromethyl benzenethiol (5 g, 28 mmol), CuI (225 mg, 3.89 mmol), ethylene glycol (3.5 g, 56.4 mmol), K2CO3 (8 g, 58 mmol) in isopropanol (20 mL) was refluxed under N2 for 12 h. The reaction mixture was filtered through a short pad of silica gel and the filtrate was concentrated in vacuo to dryness. The product was purified by flash column chromatography on silica gel to give the product 3-(2-trifluoromethyl-phenylsulfanyl)-quinoline (8.1 g, 95%)

Workup

  1. temperaturewas refluxed under N2 for 12 h
  2. filtrationThe reaction mixture was filtered through a short pad of silica gel
  3. concentrationthe filtrate was concentrated in vacuo to dryness
  4. customThe product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b2430bb01dad4bb79d198babc1790ac7
Source dataset
uspto-grants-2012_10
Patent number
US08288410B2

Reaction notes

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