Dimethylformamide → 3,5-Dibromobenzaldehyde

HRID 1657165Notes

Reaction equation

HRID 1657165 reaction equation
[Mg].Br[C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[C:5]([Br:10])[CH:4]=1.CN(C)[CH:13]=[O:14]>C(Cl)Cl>[Br:10][C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([Br:9])[CH:6]=1)[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 122791,3,5-TribromobenzeneHCID 5462224Magnesium

Product 1

HCID 6220773,5-DibromobenzaldehydeYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.344G (56 mM) of magnesium was added to a solution of 15-7G(50 mM) of 1,3,5-tribromobenzene and the mixture was stirred at room temperature after 5 hours, most of the metal was digested. To the resulting brown Grignard solution was added 7.5 mL (0.1M) of N,N-dimethylformamide at 0° under nitrogen. The resulting mixture was stirred overnight at room temperature. Solvent was removed in vacuo at room temperature. The residue was taken up in 200 mL of ethyl acetate and washed with 6×50 mL of saturated sodium chloride solution, dried over anhydrous MgSO4. Solvent was removed to give a crude solid, which was dissolved in minimum amount of CH2Cl2 and applied on silica gel. Elution with 1:9 mixture of ether:hexane containing methylene chloride gave 45% yield of the desired aldehyde as white solid.

Workup

  1. stirringThe resulting mixture was stirred overnight at room temperature
  2. customSolvent was removed in vacuo at room temperature
  3. washwashed with 6×50 mL of saturated sodium chloride solution
  4. dry with materialdried over anhydrous MgSO4
  5. customSolvent was removed
  6. customto give a crude solid, which
  7. washElution
  8. additionwith 1:9 mixture of ether
  9. additionhexane containing methylene chloride

Sources & evidence

ORD record
ord-239c12859d1b415f9dd49f69614c576d
Source dataset
uspto-grants-1993_10
Patent number
US05256777

Reaction notes

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