Ammonia → 4,5-Diethoxy-3-fluorophthalonitrile

HRID 1295949Notes

Reaction equation

HRID 1295949 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[C:5]([O:11][CH2:12][CH3:13])=[C:4]([F:14])[C:3]=1Br.[Cu](C#N)[C:17]#[N:18].N.[CH3:22][N:23](C)C=O>>[CH2:12]([O:11][C:5]1[C:4]([F:14])=[C:3]([C:22]#[N:23])[C:2](=[CH:7][C:6]=1[O:8][CH2:9][CH3:10])[C:17]#[N:18])[CH3:13]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 117098891,2-Dibromo-4,5-diethoxy-3-fluorobenzeneHCID 178418260HCID 178418260, compound

Product 1

HCID 229298414,5-Diethoxy-3-fluorophthalonitrile

Conditions

Temperature
150 °C

Procedure

After dissolving the 1,2-dibromo-4,5-diethoxy-3-fluorobenzene (480 g) in dimethylformamide (1400 ml), copper cyanide (345 g) was added and the mixture was stirred at 150° C. for 3 hours. Saturated aqueous ammonia was added to the reaction mixture, and then the mixture was stirred overnight and extraction was performed with toluene. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (513 g) as white crystals.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight
  3. extractionextraction
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f1aa9cb6fca04ca9b6398103df5a9706
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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