Trifluoroacetic acid → 4-(4-Bromo-pyridin-2-yl)-4-oxo-butyraldehyde

HRID 1034612Notes

Reaction equation

HRID 1034612 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=[O:16])[CH2:9][CH2:10][CH:11](OC)[O:12]C)[CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=[O:16])[CH2:9][CH2:10][CH:11]=[O:12])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58191758HCID 58191758, compound

Product 1

HCID 581917804-(4-Bromo-pyridin-2-yl)-4-oxo-butyraldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromo-pyridin-2-yl)-4,4-dimethoxy-butan-1-one (2) (crude from Step 2, 11 g, 38.2 mmol) in 100 of CH2Cl2 at room temperature is added trifluoroacetic acid (10.9 g, 95.4 mmol) and the reaction mixture is stirred overnight. The reaction is concentrated, the residue dissolved in ethyl acetate (150 mL) and washed with water 3 times. The organic layers are combined, dried over Na2SO4 and the solvent evaporated. The residue is purified by flash column chromatography (30% EtOAc in hexanes) to give 4-(4-bromo-pyridin-2-yl)-4-oxo-butyraldehyde (3) as an yellow oil. (4.16 g, 45%): MS ES+244.04.

Workup

  1. concentrationThe reaction is concentrated
  2. dissolutionthe residue dissolved in ethyl acetate (150 mL)
  3. washwashed with water 3 times
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated
  6. customThe residue is purified by flash column chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4a2695e74ca14d3bbbf8006355b6c42e
Source dataset
uspto-grants-2013_10
Patent number
US08546336B2

Reaction notes

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