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

HRID 1072020Notes

Reaction equation

HRID 1072020 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 655.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromine (1 7.6 g, 1 10 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-e789f4320123488aba708e9ee8341b55
Source dataset
uspto-grants-2005_06
Patent number
US06908929B2

Reaction notes

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