Tert-Butyl hypochlorite → 2-Chloro-4-(3,5-difluorophenoxy)phenol

HRID 1655440Notes

Reaction equation

HRID 1655440 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(O[Cl:22])(C)(C)C>C(Cl)(Cl)(Cl)Cl>[Cl:22][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

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 133918364-(3,5-Difluorophenoxy)phenol

Product 1

HCID 197922522-Chloro-4-(3,5-difluorophenoxy)phenolYield 91.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5.0 g of 4-(3,5-difluorophenoxy)phenol in 50 ml of carbon tetrachloride, there was added dropwise 2.45 g of t-butylhypochlorite with vigorously stirring and ice-cooling. After completion of the addition, the reaction mixture was stirred at room temperature for 5 hours and concentrated, followed by addition of 200 ml of ethyl acetate. The obtained solution was washed with an aqueous solution of 5% wt. sodium dicarbonate, dried 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. additionAfter completion of the addition
  3. stirringthe reaction mixture was stirred at room temperature for 5 hours
  4. concentrationconcentrated
  5. additionfollowed by addition of 200 ml of ethyl acetate
  6. washThe obtained solution was washed with an aqueous solution of 5% wt. sodium dicarbonate
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8aecd82e22ee411daa7fe10cfaff5f1c
Source dataset
uspto-grants-1993_10
Patent number
US05250574

Reaction notes

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