Dimethylformamide → 5-Bromopyridine-2-carbaldehyde

HRID 861003Notes

Reaction equation

HRID 861003 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Li]CCCC.CN([CH:17]=[O:18])C>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:17]=[O:18])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 98775625-Bromopyridine-2-carbaldehyde

Conditions

Temperature
-78 °C

Procedure

To a solution of 2,5-dibromopyridine (1.0 eq.) in Tol (O. 1M) at −78° C. was added n-BuLi (1.0Seq.). The mixture was stirred for 2 h at −78° C. then DMF (3.0 eq.) was added. The final mixture was stirred for 12 h at −78° C., quenched using saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1) afforded the title compound as an oil.

Workup

  1. customquenched
  2. extractionextracted with Et2O (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ef352b91ace430786465ecce04b2a05
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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