Ethanol → HCID 68764811, compound

HRID 1878624Notes

Reaction equation

HRID 1878624 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:10])[C:7]=1[CH:8]=O.[O-:11][CH2:12][CH3:13].[Na+].C([O-])(O)=O.[Na+].[CH3:20][CH2:21][OH:22]>>[CH2:12]([O:11][C:21](=[O:22])[CH:20]=[CH:8][C:7]1[C:2]([Br:1])=[CH:3][N:4]=[CH:5][C:6]=1[Br:10])[CH3:13]

Participants

5

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 27629983,5-Dibromo-4-pyridinecarboxaldehyde

Product 1

HCID 68764811HCID 68764811, compound

Procedure

3,5-Dibromo-pyridine-4-carbaldehyde (Sigma-Aldrich, St. Louis, USA) (1 eq, 15.1 mmol, 4.0 g) is suspended in EtOH (50 ml). Then triethyl phosphonoacetate (Sigma-Aldrich, St. Louis, USA) (1.1 eq, 16.6 mmol, 3.32 ml) and sodium ethoxide (21% in EtOH, 1.1 eq, 16.6 mmol, 6.12 ml) are added. The resulting mixture is stirred for 15 min at r.t., before adding sat. aqueous NaHCO3 solution. The mixture is extracted with DCM, and the organic layer is dried with MgSO4 and concentrated in vacuo. Purification by column chromatography (hexane/EtOAc) yields the title compound; [M+H]+=336.

Workup

  1. extractionThe mixture is extracted with DCM
  2. dry with materialthe organic layer is dried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-5506be7d0cc947aa89fd0dd30f8dc95f
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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