Thiophenol → 3-Bromo-5-(phenylthio)pyridine

HRID 902571Notes

Reaction equation

HRID 902571 reaction equation
[H-].[Na+].Br[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:10])[CH:9]=1.[Cl-].[NH4+].[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Br:10][C:8]1[CH:7]=[N:6][CH:5]=[C:4]([S:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 693693,5-Dibromopyridine

Product 1

HCID 231221693-Bromo-5-(phenylthio)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

In a volume of 268 μl of thiophenol was dissolved in 8 ml of dimethylformamide, added with 62.6 mg of sodium hydride at room temperature, and stirred for 1 hour. The reaction system was added with 618 mg of 3,5-dibromopyridine, heated to 130° C., and stirred under the same condition for 6.5 hours. The reaction system was added with saturated aqueous ammonium chloride, and extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate (50:1 to 7:1)) to obtain 403 mg of the title compound.

Workup

  1. stirringstirred under the same condition for 6.5 hours
  2. extractionextracted with ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate (50:1 to 7:1))

Sources & evidence

ORD record
ord-0dd67fd64f7c445e80eba1c55439e45f
Source dataset
uspto-grants-2008_04
Patent number
US07365174B2

Reaction notes

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