Ethylene Glycol → HCID 21099458, compound

HRID 2376936Notes

Reaction equation

HRID 2376936 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16].C(=O)([O-])[O-].[K+].[K+].C(O)CO>[Cu]I.O.C(O)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 5202162-FluorothiophenolHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 21099458HCID 21099458, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

2-chloro-5-iodopyridine (3.0 g, 12.5 mmol), 2-fluorobenzenethiol (1.6 g, 12.5 mmol), potassium carbonate (3.45 g, 25.0 mmol), ethylene glycol (1.55 g, 25.0 mmol) and copper(I) iodide (0.12 g, 0.63 mmol) were stirred in refluxing isopropyl alcohol (50 mL) for 40 hours. Room temperature was attained, water was added and the products extracted into ethyl acetate (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo while loading onto silica. Dry flash column chromatography using isohexane-2% ethyl acetate/isohexane gave 2-chloro-5-[(2-fluorophenyl)thio]pyridine as a pale yellow oil (2.0 g, 67%). δH (500 MHz, d6 DMSO): 7.25-7.29 (1H, m), 7.34-7.39 (1H, m), 7.44-7.51 (2H, m), 7.53 (1H, d, J=8.4 Hz), 7.75 (1H, dd, J=2.6, 8.4 Hz), 8.36 (1H, d, J=2.6 Hz); m/z (ES+) 240, 242 [MH+].

Workup

  1. customRoom temperature
  2. extractionthe products extracted into ethyl acetate (×2)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customDry flash column chromatography

Sources & evidence

ORD record
ord-05c5f7f725414f67bb913f8ba8dacd42
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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