Water → 3-Bromo-4-fluorobenzaldehyde

HRID 851284Notes

Reaction equation

HRID 851284 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[C:5]#N.[OH2:11]>[Ni].C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:11]

Participants

5

Reactant 2

HCID 962WaterHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 1736043-Bromo-4-fluorobenzaldehydeYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 284Formic AcidSolvent

Procedure

17.0 g of a 50% strength alkaline suspension of Raney nickel were filtered under a nitrogen atmosphere and the material on the filter was washed until neutral. The Raney nickel obtained by this method was suspended in 150 ml of formic acid. 20.0 g (0.1 mole) of 3-bromo-4-fluoro-benzonitrile were added to this suspension. The mixture was heated at 80° to 90° C. for 3 to 5 hours and the reaction mixture was then cooled and poured into 300 ml of water. After filtering, the filtrate was twice extracted with, in each case, 200 ml of toluene. The toluene phase was dried over sodium sulphate and then concentrated. 17.2 g (85% of theory) of 3-bromo-4-fluoro-benzaldehyde with a boiling point of 63°-65° C./0.3 mm Hg were obtained.

Workup

  1. filtrationwere filtered under a nitrogen atmosphere
  2. washthe material on the filter was washed until neutral
  3. customThe Raney nickel obtained by this method
  4. temperatureThe mixture was heated at 80° to 90° C. for 3 to 5 hours
  5. temperaturethe reaction mixture was then cooled
  6. filtrationAfter filtering
  7. extractionthe filtrate was twice extracted with, in each case, 200 ml of toluene
  8. dry with materialThe toluene phase was dried over sodium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a7d4e6788f22427e80515f37aff1301f
Source dataset
uspto-grants-1983_05
Patent number
US04383949

Reaction notes

Loading…