Ethyl Acetate → 5-Bromo-2-(methylsulfinyl)pyridine

HRID 1046242Notes

Reaction equation

HRID 1046242 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.C(OCC)(=[O:12])C>O.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH3:9])=[O:12])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 114242515-Bromo-2-(methylthio)pyridine

Product 1

HCID 584853485-Bromo-2-(methylsulfinyl)pyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

NalO4 (0.52 g) dissolved in water (0.5 mL) was added to a solution of 5-bromo-2-methylsulfanyl-pyridine (0.25 g) in acetic acid (3 mL) at room temperature. The resulting mixture was stirred at room temperature overnight. Then, water and ethyl acetate were added and the mixture was stirred for another 10 min. The organic phase was separated and washed with 10% aqueous Na2S2O3 solution, 10% aqueous K2CO3 solution, and brine. After drying (MgSO4), the solvent was evaporated to afford the title compound. Yield: 0.20 g (72% of theory); Mass spectrum (ESI+): m/z=220/222 (Br) [M+H]+.

Workup

  1. stirringthe mixture was stirred for another 10 min
  2. customThe organic phase was separated
  3. washwashed with 10% aqueous Na2S2O3 solution, 10% aqueous K2CO3 solution, and brine
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-deb7fa39ccb74c9b86cd34a40cf2f002
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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