4-Phenoxyphenol → 2-Fluoro-4-phenoxyphenol

HRID 479646Notes

Reaction equation

HRID 479646 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]S(C(F)(F)[F:20])(=O)=O.ClC1C=[N+](F)C=C(Cl)C=1>ClCCl>[F:20][C:10]1[CH:9]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][C:11]=1[OH:14]

Participants

4

Reactant 2

HCID 132544-PhenoxyphenolHCID 27245783,5-Dichloro-1-fluoropyridinium triflate

Product 1

HCID 114697662-Fluoro-4-phenoxyphenolYield 14.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 250 ml dichloromethane solution of 4-phenoxyphenol (2 g, 10.7 mmol) was added 3,5-dichloro-1-fluoro-pyridinium triflate (4.14 g, 13.1 mmol). After heating to reflux for 1 hr, the solvent was removed, the crude product was diluted with AcOEt and sat. bicarb. solution. The organic layer was separated, dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Elution with 10% methy t-butyl ether/hexanes gave 312 mg of the title compound as a pale yellow oil.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 1 hr
  3. customthe solvent was removed
  4. additionthe crude product was diluted with AcOEt and sat. bicarb
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel
  10. washElution with 10% methy t-butyl ether/hexanes

Sources & evidence

ORD record
ord-08107118c1c747118a46f81b0a91fd72
Source dataset
uspto-grants-2003_11
Patent number
US06645997B2

Reaction notes

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