Dimethyl Sulfoxide → 3-Bromo-4-(oxiran-2-yl)pyridine

HRID 1253943Notes

Reaction equation

HRID 1253943 reaction equation
[SH3+].[H-].[Na+].[Br:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[CH:11]=[O:12].[CH3:13]S(C)=O>>[Br:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[CH:11]1[CH2:13][O:12]1

Participants

5

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 27629973-Bromopyridine-4-carboxaldehydeHCID 3015009Sulfonium

Product 1

HCID 866633603-Bromo-4-(oxiran-2-yl)pyridine

Procedure

To a solution of sulfonium salt (7.39 g, 33.6 mmol) in DMSO (40 mL) was added sodium hydride (60% in oil, 1.236 g, 30.9 mmol) at room temperature. After 15 min of stirring, 3-Bromo-pyridine-4-carbaldehyde (930 mg, 5 mmol) in DMSO (20 was added slowly at this temperature. After addition, the resulting mixture was stirred for another 30 min, and was subsequently quenched with brine. The mixture was extracted with ethyl acetate twice. The combined extracts were dried over anhydrous Na2SO4. After filtration and concentration, the title compound was obtained (200 mg).

Workup

  1. additionAfter addition
  2. stirringthe resulting mixture was stirred for another 30 min
  3. customwas subsequently quenched with brine
  4. extractionThe mixture was extracted with ethyl acetate twice
  5. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  6. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-4b88c29e3b574b46818aa8c3007e31fc
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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