4-Bromophenol → 4-(4-Bromophenoxy)benzonitrile

HRID 432190Notes

Reaction equation

HRID 432190 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C1OCCOCCOCCOCCOCCOC1.[F-].[K+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 145174-FluorobenzonitrileHCID 2855718-Crown-6HCID 522689Potassium Fluoride

Product 1

HCID 223473964-(4-Bromophenoxy)benzonitrileYield 51.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-bromophenol (4.56 g, 0.0264 mol), 4-fluorobenzonitrile (0.0264 mol), 18-crown-6 (0.7 g, 0.00264 mol) and 40% potassium fluoride on alumina (10.8 g) in anhydrous acetonitrile (100 mL) was heated at reflux under an atmosphere of nitrogen for twelve hours. It was cooled to ambient temperature, filtered through a Celite pad and concentrated under reduced pressure. The residue was partitioned between diethyl ether (120 mL) and water (100 mL), the organic phase was further washed with saturated solution of potassium chloride in water, dried with magnesium sulfate and concentrated. The residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (3:97) as mobile phase to yield 4-(4-bromophenoxy)benzonitrile (3.7 g, 0.0135 mol) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of nitrogen for twelve hours
  3. filtrationfiltered through a Celite pad
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between diethyl ether (120 mL) and water (100 mL)
  6. washthe organic phase was further washed with saturated solution of potassium chloride in water
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-ba74ae2d2f2f455a95682fecb7347374
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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