4'-Hydroxyacetophenone → 2-Bromo-1-(4-hydroxyphenyl)ethanone

HRID 2296732Notes

Reaction equation

HRID 2296732 reaction equation
[Br:1]Br.[CH3:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)=[O:5].C(=O)(O)[O-].[Na+]>CCOCC>[CH:7]1[C:6]([C:4]([CH2:3][Br:1])=[O:5])=[CH:11][CH:10]=[C:9]([OH:12])[CH:8]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneYield 59.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromine (17.6 g, 110 mmol) was added dropwise to a 0° C. solution of 4-hydroxyacetophenone (15 g, 110 mmol) in ether (200 mL) over 20 minutes. The mixture was stirred for 1 hour and poured carefully into saturated sodium bicarbonate solution (500 mL). The organics were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo. The crude product was then recrystallized from ether to afford the title compound (14.1 g).

Workup

  1. washThe organics were washed with saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was then recrystallized from ether

Sources & evidence

ORD record
ord-f17c76b2f274472e8151bc168c688cee
Source dataset
uspto-grants-2002_12
Patent number
US06489337B1

Reaction notes

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