Dimethylformamide → 3,5-diiodobenzaldehyde

HRID 1741582Notes

Reaction equation

HRID 1741582 reaction equation
I[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[CH:3]=1.C([Li])CCC.CN(C)[CH:17]=[O:18]>CCOCC.C(OCC)(=O)C>[I:9][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([I:8])[CH:5]=1)[CH:17]=[O:18]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 12282Benzene, 1,3,5-triiodo-HCID 178418339Butyllithium

Product 1

HCID 102370743,5-diiodobenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of 1,3,5-triiodobenzene (7.5 G, 16.4 mM) in 72 mL of ether at -78° was added n-butyllithium 7.2 mL; 18 mM). After 15 minutes of stirring, 2.8 mL (36 mM) of N,N-dimethylformamide was added dropwise and the reaction mixture was stirred overnight. After diluting with 100 mL of ethyl acetate, the reaction mixture was washed with 3×50 mL of saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. Solvent removal gave a crude product, which was chromatographed on silica gel (application in minimum amount of CH2Cl2 ; and elution with 1:9 EtOAc:hexane) to yield 1.3 G of the desired aldehyde as cream colored solid.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. washthe reaction mixture was washed with 3×50 mL of saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customSolvent removal
  5. customgave a crude product, which
  6. customwas chromatographed on silica gel (application in minimum amount of CH2Cl2 ; and elution with 1:9 EtOAc:hexane)

Sources & evidence

ORD record
ord-abc919bca6224fa5b13cfcc748b258cc
Source dataset
uspto-grants-1994_08
Patent number
US05334590

Reaction notes

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