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

HRID 45776

Reaction equation

HRID 45776 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-f59ca2945eba4b08beec8ffdabe7efe7
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Linked notes

Loading…