Dimethylformamide → 6-Bromo-3-pyridinecarboxaldehyde

HRID 640537Notes

Reaction equation

HRID 640537 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.C([Li])CCC.CN(C)[CH:16]=[O:17]>C(OCC)C>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH:16]=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 117692346-Bromo-3-pyridinecarboxaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a diethyl ether (500 mL) solution of 2,5-dibromopyridine (25 g, 110 mmol) was added dropwise n-butyl lithium (2.67 M n-hexane solution, 45 mL, 120 mmol) at −76° C., which was stirred for 25 minutes. To this solution was added dropwise N,N-dimethylformamide (9.0 mL, 120 mmol) at −76° C. Upon completion of this addition, the reaction solution was gradually cooled to room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1) to obtain the title compound (8.0 g, 41%).

Workup

  1. additionUpon completion of this addition
  2. customThis mixture was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-ede6a59e6b404e8ebb94d8807101d4ad
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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