Water → 3,4-Difluoro-5-formylbenzonitrile

HRID 34023Notes

Reaction equation

HRID 34023 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:11])[C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Cu](C#N)[C:13]#[N:14].C(OCC)(=O)C.O>CN1CCCC1=O>[F:11][C:4]1[CH:3]=[C:2]([CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[F:10])[C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 230701825-Bromo-2,3-difluorobenzaldehydeHCID 178418260HCID 178418260, compound

Product 1

HCID 230702283,4-Difluoro-5-formylbenzonitrileYield 42.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 10.0 g of 5-bromo-2,3-difluorobenzaldehyde in 40.0 mL of 1-methyl-2-pyrrolidone was added 4.26 g of copper cyanide (I) at room temperature and stirred at 170° C. for 8 hours. Adding ethyl acetate and water, the solution was stirred, and insoluble substances were filtered out through celite. The organic layer of filtrate was washed successively with saturated aqueous ammonium chloride, water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:20), to afford 2.64 g of the title compound as colorless crystals.

Workup

  1. filtrationinsoluble substances were filtered out through celite
  2. washThe organic layer of filtrate was washed successively with saturated aqueous ammonium chloride, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:20)

Sources & evidence

ORD record
ord-4c1e5206dc544587b892eaf2c3a9dbe2
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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