Ammonia → 3,4-Diethoxy-2-fluorobenzonitrile

HRID 2223755Notes

Reaction equation

HRID 2223755 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[C:7]([O:14][CH2:15][CH3:16])[C:6]=1[F:17].C(OCC)(=O)C.N>CN(C)C=O>[CH2:15]([O:14][C:7]1[C:6]([F:17])=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH2:12][CH3:13])[C:2]#[N:3])[CH3:16]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 230937081-Bromo-3,4-diethoxy-2-fluorobenzeneHCID 178418546HCID 178418546, compound

Product 1

HCID 230937173,4-Diethoxy-2-fluorobenzonitrileYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

Copper(I)cyanide (6.8 g, 68.3 mmol) was added to a solution of 1-bromo-3,4-diethoxy-2-fluorobenzene (12.0 g, 45.6 mmol) in N,N-dimethylformamide (DMF) (60 mL) at room temperature, and this was then stirred at 155° C. for 3 hours. The reaction solution was cooled on ice. Following addition of ethyl acetate and 28% aqueous ammonia, the organic layer was separated and washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was removed after filtration, and the residue was purified by silica gel column chromatography (n-hexane, ethyl acetate) to give 9.0 g of the subject compound (yield: 94.3%).

Workup

  1. temperatureThe reaction solution was cooled on ice
  2. customthe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. filtrationafter filtration
  7. customthe residue was purified by silica gel column chromatography (n-hexane, ethyl acetate)

Sources & evidence

ORD record
ord-658744872cee4cc89b01c6b862acc909
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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