Dimethylformamide → 6-Bromopyridine-2-carbaldehyde

HRID 1272514Notes

Reaction equation

HRID 1272514 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[Li]CCCC.CN([CH:17]=[O:18])C>C1COCC1>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:17]=[O:18])[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 122742,6-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 27570096-Bromopyridine-2-carbaldehydeYield 28.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.0 g (21.2 mmol) of 2,6-dibromopyridine in THF at −78° C. was added 9.2 mL (21 mmol) of 2.3 M solution of n-BuLi in hexanes, followed by 2.3 mL (30 mmol) of DMF. The mixture was stirred for 45 min in the cold, quenched with saturated NaHCO3, extracted with ethyl acetate and the product purified by column chromatography (3% ethyl acetate in hexanes) to furnish 1.13 g of 2-bromo-6-formylpyridine.

Workup

  1. customquenched with saturated NaHCO3
  2. extractionextracted with ethyl acetate
  3. customthe product purified by column chromatography (3% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c50818d69769468ea0f7fcd44188dbf9
Source dataset
uspto-grants-2007_04
Patent number
US07208602B2

Reaction notes

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