2,5-Dibromopyridine → 5-Bromo-2-(methylthio)pyridine

HRID 1484407Notes

Reaction equation

HRID 1484407 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][S-:10].[Na+]>CN(C=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([S:10][CH3:9])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 693532,5-DibromopyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 114242515-Bromo-2-(methylthio)pyridineYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-Dibromo-pyridine (6 g, 25.327 mmol) in DMF (60 mL) is added sodium thiomethoxide (1.95 g, 27.86 mmol) at 0° C. Reaction mixture is allowed to come to room temperature and resulting reaction mixture is stirred at room temperature for 12 h. Reaction mixture is quenched with water and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by column chromatography using silica (100-200) mesh size and using 4% ethyl acetate in hexane as an eluent to get (4.5 g) of yellow solid title compound. 1H-NMR (400 MHz, DMSO) δ: 2.49 (s, 3H), 7.29 (d, 1H, J=8.76 Hz), 7.85-7.88 (dd, 1H, J1=2.44 Hz, J2=8.48 Hz), 8.55 (d, 1H, J=2.4 Hz). LC-MS (m/z): M+H=206.1.

Workup

  1. customReaction mixture
  2. customto come to room temperature
  3. customresulting
  4. customreaction mixture
  5. customReaction mixture
  6. customis quenched with water
  7. extractionextracted with ethyl acetate
  8. dry with materialOrganic layer is dried over sodium sulphate
  9. concentrationconcentrated
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-b1287e1075c7471bbc2889889669dd82
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

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