5-Bromo-2-fluorobenzaldehyde → 5-Cyano-2-fluorobenzaldehyde

HRID 1726118Notes

Reaction equation

HRID 1726118 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:11]([Cu])#[N:12]>CN(C=O)C.Cl.O>[C:11]([C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8])#[N:12]

Participants

6

Reactant 2

HCID 7363275-Bromo-2-fluorobenzaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 109097255-Cyano-2-fluorobenzaldehydeYield 75%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of 5-bromo-2-fluorobenzaldehyde (9.2 g, 45 mmol) in DMF (5 mL) was added CuCN (4.8 g, 54 mmol) and the mixture was heated at 100° C. for 2 hours and at 130° C. overnight. The mixture was cooled to room temperature, added to a solution of FeCl2 (11 g) in conc. HCl (100 mL) and H2O (500 mL) and stirred at room temperature for 30 minutes. The aqueous was extracted with CH2Cl2 (4×200 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified to afford 5-cyano-2-fluorobenzaldehyde as a yellow solid (5.0 g, 75%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous was extracted with CH2Cl2 (4×200 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified

Sources & evidence

ORD record
ord-40fcc7b25870468b9bab3e502a023ddc
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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