Water → HCID 18426809, compound

HRID 1281151Notes

Reaction equation

HRID 1281151 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](Br)=[C:4]([CH3:10])[N:3]=1.C([Mg]Cl)(C)C.CN(C)[CH:18]=[O:19].O>O1CCCC1>[Br:1][C:2]1[N:3]=[C:4]([CH3:10])[C:5]([CH:18]=[O:19])=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8172152,5-dibromo-3,6-dimethylpyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 18426809HCID 18426809, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5-dibromo-3,6-dimethylpyridine (989 mg, 3.75 mmol) in tetrahydrofuran (6 mL) was added isopropylmagnesium chloride (2 mol/L in tetrahydrofuran; 2.0 mL, 4.0 mmol) under nitrogen atmosphere, and the mixture was stirred at room temperature for 1.5 h. Dimethylformamide (0.58 mL, 7.5 mmol) was added, and the mixture was stirred for additional 10 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (7:1 hexane/ethyl acetate) to afford 6-bromo-2,5-dimethyl-3-pyridinecarboxaldehyde (381 mg, 47%).

Workup

  1. stirringthe mixture was stirred for additional 10 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (7:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3153d1c4b84a4d739c8765d1abaa6425
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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