4-Fluorophenol → 1,3-Dibromo-5-(4-fluorophenoxy)benzene

HRID 53324

Reaction equation

HRID 53324 reaction equation
[H-].[Na+].Br[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([Br:11])[CH:5]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.[H][H]>N1C(C)=CC(C)=CC=1C>[Br:10][C:8]1[CH:9]=[C:4]([O:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH:5]=[C:6]([Br:11])[CH:7]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 122791,3,5-TribromobenzeneHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 199624081,3-Dibromo-5-(4-fluorophenoxy)benzeneYield 32.5%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

Sodium hydride (3.24 g of 60% suspension in mineral oil was added portionwise to a stirred mixture of 1,3,5-tribromobenzene (76.4 g), 4-fluorophenol (18.16 g), and cuprous oxide (11.6 g) in collidine (400 ml) at room temperature. When evolution of hydrogen had ceased the mixture was heated under reflux with stirring for 8 hours. It was then cooled and filtered. The residue was washed with ethyl acetate followed by concentrated aqueous ammonia, and the combined filtrate and washings were partitioned between ethyl acetate and water. The organic layer was washed twice with brine and evaporated. The residue was dissolved in ethyl acetate, and the solution was filtered, washed several times with citric acid solution and dried (MgSO4). The solvent was evaporated, and the residue was dissolved in hot hexane. The solution was filtered and the filtrate was evaporated. The residue was chromatographed on silica using hexane as eluent to give the title compound as an oil (18.21 g), Rf 0.31(SS 2). Found: C,41.71; H,1.97. C12H7Br2FO requires C,41.66; H,2.04%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. washThe residue was washed with ethyl acetate
  6. customthe combined filtrate and washings were partitioned between ethyl acetate and water
  7. washThe organic layer was washed twice with brine
  8. customevaporated
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. filtrationthe solution was filtered
  11. washwashed several times with citric acid solution
  12. dry with materialdried (MgSO4)
  13. customThe solvent was evaporated
  14. dissolutionthe residue was dissolved in hot hexane
  15. filtrationThe solution was filtered
  16. customthe filtrate was evaporated
  17. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-32300b7feb6546f497fbc93c293e789c
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Linked notes

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