4-(3,5-Difluorophenoxy)phenol → 2-Chloro-4-(3,5-difluorophenoxy)phenol

HRID 5207Notes

Reaction equation

HRID 5207 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:16])[CH:15]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([ClH:21]O)(C)(C)C>C(Cl)(Cl)(Cl)Cl>[Cl:21][C:8]1[CH:7]=[C:6]([O:5][C:4]2[CH:3]=[C:2]([F:1])[CH:15]=[C:14]([F:16])[CH:13]=2)[CH:11]=[CH:10][C:9]=1[OH:12]

Participants

3

Reactant 1

HCID 133918364-(3,5-Difluorophenoxy)phenol

Product 1

HCID 197922522-Chloro-4-(3,5-difluorophenoxy)phenol

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5.0 g p-(3,5-difluorophenoxy)phenol in 50 mg of carbon tetrachloride, there were added dropwise 2.45 of tert-butylhypochlorous acid with stirring and ice-cooling, and stirring was continued at room temperature for 5 hours. The reaction mixture was concentrated and extracted with 200 ml of ethyl acetate. The extract was washed with 5% aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 5.31 g of 2-chloro-4-(3,5-difluorophenoxy)phenol. Yield, 92%. nD25 : 1.5639

Workup

  1. temperatureice-cooling
  2. stirringstirring
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with 200 ml of ethyl acetate
  5. washThe extract was washed with 5% aqueous solution of sodium bicarbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11045075c0464d549a020ace23fc45e9
Source dataset
uspto-grants-1993_09
Patent number
US05243087

Reaction notes

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