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

HRID 1824525Notes

Reaction equation

HRID 1824525 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-a98913adaef7499f9e385c33702f5114
Source dataset
uspto-grants-2006_05
Patent number
US07041828B2

Reaction notes

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