Water → 6-Bromo-2-methoxynicotinaldehyde

HRID 70552Notes

Reaction equation

HRID 70552 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5](I)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:18]=[O:19].O>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:18]=[O:19])=[C:6]([O:8][CH3:9])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 582361006-bromo-3-iodo-2-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 122692136-Bromo-2-methoxynicotinaldehydeYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 6-bromo-3-iodo-2-methoxypyridine (1.0 g) in diethyl ether (38 mL) was cooled to −80° C. in a nitrogen atmosphere, and n-butyllithium (2.6 M, 0.735 mL) were added dropwise. After stirring at the same temperature for one hour, N,N-dimethylformamide (0.62 mL) was added dropwise. The mixture was stirred at the same temperature for one hour and water was added to the reaction system, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=94:6→9:1) to give 6-bromo-2-methoxynicotinaldehyde as a colorless powder (618 mg, 90%).

Workup

  1. additionwere added dropwise
  2. stirringThe mixture was stirred at the same temperature for one hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customafter which the solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=94:6→9:1)

Sources & evidence

ORD record
ord-8dbfcbe0ff0b494b903a67d4f08dfde8
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…