Nitric Acid → 3-Bromo-4-fluorobenzaldehyde

HRID 231317Notes

Reaction equation

HRID 231317 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][OH:6].[N+]([O-])(O)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6]

Participants

5

Procedure

10.2 g (0.05 mol) of 3-bromo-4-fluoro-benzyl alcohol were added to a mixture of 10 g of nitric acid (density: 1.4) and 5 ml of water at 30°-35° C. and the mixture was then stirred at room temperature for 5 hours. After adding 30 g of ice, sodium hydroxide solution was added to the mixture until the pH value reached 13, and the mixture was then extracted by shaking with 200 ml of toluene. The organic phase was washed three times with 50 ml of water each time, dried over sodium sulphate and then evaporated. The residue was distilled. 6.1 g (60% of theory) of 3-bromo-4-fluoro-benzaldehyde were thus obtained in the form of an oil which slowly solidified and had a melting point of 29°-31° C.

Workup

  1. additionwas added to the mixture until the pH value
  2. extractionthe mixture was then extracted
  3. stirringby shaking with 200 ml of toluene
  4. washThe organic phase was washed three times with 50 ml of water each time
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-26f897e62d8f4f3bb4525cd3a98f97ae
Source dataset
uspto-grants-1989_07
Patent number
US04845249

Reaction notes

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