Phenol → 4-Bromo-2-phenoxybenzoic acid

HRID 1987933Notes

Reaction equation

HRID 1987933 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4](Cl)[CH:3]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.F[P-](F)(F)(F)(F)F.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 9886HexafluorophosphateHCID 10796Cesium carbonateHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 230539204-Bromo-2-phenoxybenzoic acidYield 100.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-2-chloro-benzoic acid (10 g, 42 mmol), phenol (4.19 g, 44 mmol), tetrakisacetonitrilecopper hexafluorophosphate (3.95 g, 10.6 mmol), and cesium carbonate (27.6 g, 85 mmol) were added to a 1 L 3-neck round bottom flask equipped with a mechanical stirrer, reflux condenser, and containing toluene (350 mL). The reaction was refluxed overnight under nitrogen with stirring. After cooling, ethyl acetate (200 mL) was added and the reaction was acidified with aqueous 2N HCI. The organic phase was separated, dried (MgSO4), and filtered. The filtrate was concentrated to afford 4-bromo-2-phenoxybenzoic acid (12.4 g) that was used in subsequent reactions without further purification.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction was refluxed overnight under nitrogen
  4. temperatureAfter cooling
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5fa9b213f5b943538871fa8bea49f88a
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

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