Hydrogen Bromide → 4-(3,5-Difluorophenoxy)phenol

HRID 1638304Notes

Reaction equation

HRID 1638304 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([F:17])[CH:16]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][CH:7]=1.Br>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([F:17])[CH:16]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 134559274-(3,5-Difluorophenoxy)anisole

Product 1

HCID 133918364-(3,5-Difluorophenoxy)phenolYield 98.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(3,5-difluorophenoxy)anisole (22.0 g, 0.093 mol), acetic acid (200 ml) and a 47% aqueous hydrogen bromide solution (200 ml) was heated with stirring under reflux for 8 hours. After allowed to cool, the reaction mixture was poured into ice-water and extracted with a mixture of ether and n-hexane (1:2). The organic layer was washed with water three times and dried over anhydrous magnesium sulfate. Removal of the solvent gave 4-(3,5-difluorophenoxy)phenol (20.27 g).

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureto cool
  3. extractionextracted with a mixture of ether and n-hexane (1:2)
  4. washThe organic layer was washed with water three times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-c0b1974e886545e0a42bd4d8663d6dd1
Source dataset
uspto-grants-1989_11
Patent number
US04879292

Reaction notes

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