Dimethylformamide → 5-bromo-2-(phenylthio)pyridine

HRID 78082Notes

Reaction equation

HRID 78082 reaction equation
CN(C)C=O.[C:6]1([SH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[Na+].Br[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=1>O>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([S:12][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 221806675-bromo-2-(phenylthio)pyridineYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide (20 mL) solution of thiophenol (1.02 g, 9.28 mmol) was added sodium hydride (446 mg, 9.28 mmol, 50% in oil), which was stirred for 15 minutes at room temperature. 2,5-Dibromopyridine (2.00 g, 8.44 mmol) was then added to this reaction mixture and stirred for 35 minutes at room temperature, and then for a further 45 minutes at 55° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane: ethyl acetate:=4:1) to obtain the title compound (2.24 g, quant.).

Workup

  1. stirringstirred for 35 minutes at room temperature
  2. waitfor a further 45 minutes at 55° C
  3. extractionwhich was then extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (heptane: ethyl acetate:=4:1)

Sources & evidence

ORD record
ord-0ccdee8077d14f558e500e23e61d34dc
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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