Thiophenol → 2-Chloro-5-(phenylthio)pyridine

HRID 45241

Reaction equation

HRID 45241 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[O-].[Na+]>CO.[OH-].[Na+].[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 7969ThiophenolHCID 43971762-Chloro-5-iodopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 111953972-Chloro-5-(phenylthio)pyridineYield 60%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.4 g (14.3 mmol) of 2-chloro-5 iodopyridine, 1.9 g (17.2 mmol) of thiophenol, 0.93 g (17.2 mmol) of sodium methoxide and 0.36 g (5.7 mmol) of copper in 18 mL of MeOH is heated for 12 hours at 80° C. After cooling to room temperature, the medium is taken up in 100 mL of 1N NaOH and the MeOH is evaporated off under reduced pressure. The reaction medium is extracted with EtOAc (2×100 mL), the organic phase is washed with 0.1N NaOH (2×30 mL), and then dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc mixture (8/2). 1.90 g of 2-chloro-5-(phenylsulfanyl)pyridine are obtained in the form of a white powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe MeOH is evaporated off under reduced pressure
  3. extractionThe reaction medium is extracted with EtOAc (2×100 mL)
  4. washthe organic phase is washed with 0.1N NaOH (2×30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by chromatography on a column of silica gel
  8. washeluting with a cyclohexane/EtOAc mixture (8/2)

Sources & evidence

ORD record
ord-54549360e77f43089666cb6f25cc9bf9
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Linked notes

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