Dimethylformamide → 3,5-Dibromobenzaldehyde

HRID 487068Notes

Reaction equation

HRID 487068 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.[Mg].CN([CH:14]=[O:15])C>C1COCC1.C(Cl)Cl>[Br:9][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([Br:8])[CH:5]=1)[CH:14]=[O:15]

Participants

6

Reactant 3

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

Product 1

HCID 6220773,5-Dibromobenzaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15.7 g (50 mmoles) of 1,3,5-tribromobenzene and 1.344 g (56 mmoles) of magnesium in 200 mL of THF was stirred 5 hrs. At room temperature 7.5 mL (100 mmoles) of DMF was then added at 0° and the reaction mixture was stirred overnight. 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 satd. sodium chloride soln. The organic phase was dried over anhyd. MgSO4. Solvent was removed to give a crude solid, which was dissolved in minimum amount of methylene chloride, and applied on silica gel. Elution with 1:9 mixture of ether:hexane mixture containing 3% methylene chloride gave the desired 3,5-dibromobenzaldehyde as white solid.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customSolvent was removed in vacuo at room temperature the residue
  3. washwashed with 6×50 mL of satd
  4. customThe organic phase was dried over anhyd
  5. customSolvent was removed
  6. customto give a crude solid, which
  7. washElution
  8. additionwith 1:9 mixture of ether
  9. additionhexane mixture containing 3% methylene chloride

Sources & evidence

ORD record
ord-700407071c2541758eb64e8c668e02f7
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

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