Water → 5-Bromo-4-methylpicolinaldehyde

HRID 1027593Notes

Reaction equation

HRID 1027593 reaction equation
C([Mg]Br)(C)C.CN(C)[CH:8]=[O:9].O.[Br:12][C:13]1[C:14]([CH3:20])=[CH:15][C:16](I)=[N:17][CH:18]=1>O1CCCC1>[Br:12][C:13]1[C:14]([CH3:20])=[CH:15][C:16]([CH:8]=[O:9])=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 263699285-Bromo-2-iodo-4-methylpyridineHCID 178418365HCID 178418365, compound

Product 1

HCID 594745005-Bromo-4-methylpicolinaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

In an oven-dried flask the compound obtained in Step A (4.67 g) was dissolved in tetrahydrofuran (22 ml). The solution was cooled to −15° C., then isopropyl magnesium bromide (17.2 ml, 15% solution in THF) was added dropwise at a rate to keep the internal temperature between −15° C. to −10° C. The reaction was stirred at this temperature for 1 hour, then anhydrous dimethylformamide (1.8 ml) was added at a rate to keep the internal temperature below 0° C. The reaction was stirred at this temperature for 1 hour, then poured into water and extracted with diethyl ether. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude title aldehyde product (2.4 g, brown solid) was used as such in the next step.

Workup

  1. custombetween −15° C. to −10° C
  2. customthe internal temperature below 0° C
  3. stirringThe reaction was stirred at this temperature for 1 hour
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ed6e1dabaa34aa886e05050e644ba6b
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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