Dimethylformamide → 5-Bromo-3-pyridinecarboxaldehyde

HRID 861013Notes

Reaction equation

HRID 861013 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[Li]CCCC.CN([CH:17]=[O:18])C>CCOCC>[Br:8][C:6]1[CH:7]=[C:2]([CH:17]=[O:18])[CH:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 693693,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 27847345-Bromo-3-pyridinecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3,5-dibromopyridine (1.0 eq.) in Et2O (0.1M) at −78° C. was added n-BuLi (1.05 eq.). The mixture was stirred for 30 min at −78° C. then DMF (3.0 eq.) was added. The final mixture was warmed to rt, stirred for 3 h, quenched using saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 4:1) afforded the title compound as an oil.

Workup

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

Sources & evidence

ORD record
ord-728600b0e21e418eb656e96e9dca9c6e
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

Loading…