6-Bromo-2-naphthalenol → HCID 22380948, compound

HRID 895716Notes

Reaction equation

HRID 895716 reaction equation
F[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17]2.C1OCCOCCOCCOCCOCCOC1>C(#N)C>[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([O:24][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH:18]=[CH:17]2

Participants

5

Reactant 3

HCID 271446-Bromo-2-naphthalenolHCID 2855718-Crown-6HCID 27590482-Fluoro-4-nitrobenzonitrile

Product 1

HCID 22380948HCID 22380948, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After heating to reflux 2-fluoro-4-nitrobenzonitrile (1 g), 6-bromo-2-naphthol (1.41 g), potassium fluoride/alumina (0.7 g) and 18-crown-6 (0.16 g) in acetonitrile, the mixture was reacted for 12 hours. It was then cooled to room temperature, the insoluble portion was filtered using celite, the ethyl acetate layer was washed with water and saturated saline and then dried over magnesium sulfate, and the solvent was distilled off. Methanol was added to the residue for crystallization to obtain 1.43 g of 2-(6-bromo-2-naphthyloxy)-4-nitrobenzonitrile.

Workup

  1. temperatureAfter heating
  2. customthe mixture was reacted for 12 hours
  3. filtrationthe insoluble portion was filtered
  4. washthe ethyl acetate layer was washed with water and saturated saline
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. additionMethanol was added to the residue for crystallization

Sources & evidence

ORD record
ord-64ede36cf3d745eda295814b4cd5bad6
Source dataset
uspto-grants-2005_07
Patent number
US06916837B2

Reaction notes

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