1,4-Dibromonaphthalene → 4-Bromo-1-naphthonitrile

HRID 470384Notes

Reaction equation

HRID 470384 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][CH:3]=1.[Cu](C#N)[C:14]#[N:15]>CN(C=O)C>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:14]#[N:15])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 665211,4-DibromonaphthaleneHCID 178418260HCID 178418260, compound

Product 1

HCID 146621114-Bromo-1-naphthonitrileYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 1,4-dibromonaphthalene (24.06 g, 84 mmol) and copper cyanide (6.02 g, 67 mmol) in DMF (85 mL) was heated to 125° C. overnight. The mixture was partially concentrated to remove DMF and the resulting residue washed with aqueous ammonium hydroxide and extracted with ethyl acetate. The organic layer was concentrated and purified by chromatography to yield 4-bromo-1-naphthonitrile (5.13 g, 26%).

Workup

  1. concentrationThe mixture was partially concentrated
  2. customto remove DMF
  3. washthe resulting residue washed with aqueous ammonium hydroxide
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-b8f2aa8ea3b8477c9210ea6ab9c410ac
Source dataset
uspto-grants-2014_01
Patent number
US08629278B2

Reaction notes

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