Ethanol → 4-Bromo-3-formylbenzonitrile

HRID 554589Notes

Reaction equation

HRID 554589 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:10](Br)Br.CC[OH:15]>O.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:10]=[O:15]

Participants

5

Reactant 2

HCID 702EthanolHCID 159400004-Bromo-3-(dibromomethyl)benzonitrile

Product 1

HCID 225749024-Bromo-3-formylbenzonitrile

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-Bromo-3-dibromomethyl-benzonitrile (5.66 g, 16 mmol) was dissolved in EtOH (150 mL) and heated to 60° C. Silver nitrate (6.80 g, 40 mmol), prepared as a solution in H2O (40 mL), was added dropwise, and the reaction was heated to 75° C. and stirred overnight. The organic layer was decanted, concentrated, and filtered, and the residue was partitioned between EtOAc and H2O. The product was extracted with EtOAc, and the combined organic layers were concentrated and purified by silica gel chromatography (0-30% EtOAc in hexanes) to give 4-bromo-3-formyl-benzonitrile.

Workup

  1. additionwas added dropwise
  2. temperaturethe reaction was heated to 75° C.
  3. customThe organic layer was decanted
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customthe residue was partitioned between EtOAc and H2O
  7. extractionThe product was extracted with EtOAc
  8. concentrationthe combined organic layers were concentrated
  9. custompurified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f229cff590ee43e1bebf441db5d35dfd
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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