Hydrogen Bromide → 2-Bromo-1-(4-hydroxyphenyl)ethanone

HRID 1977303Notes

Reaction equation

HRID 1977303 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[BrH:11].[NH+]1C=CC=CC=1.Br>C(O)(=O)C>[Br:11][CH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 74694'-HydroxyacetophenoneHCID 21226041Pyridinium hydrobromide

Product 1

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-hydroxyacetophenone (10 g) and pyridinium hydrobromide perbromide (23.5 g) in acetic acid (80 ml) was added hydrogenbromide (30% in acetic acid solution) (40 ml) and the mixture was stirred overnight at ambient temperature. The reaction mixture was added to ice water and extracted with ethyl acetate. The organic layer was taken and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to afford 2-bromo-1-(4-hydroxyphenyl)ethanone (1.72 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationMagnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4fc888289fb742ed8fb883b1129dbef2
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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