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

HRID 10787

Reaction equation

HRID 10787 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[Br:11]Br>O1CCOCC1>[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

4

Reactant 2

HCID 74694'-HydroxyacetophenoneHCID 24408Bromine

Product 1

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneYield 44%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 4-hydroxyacetophenone (2.5 g, 18.3 mmol) (Aldrich) in dioxane (10 mL) was added dropwise a solution of bromine (3.22 g, 20.1 mmol) in dioxane (20 mL). After stirring for 10 minutes, the mixture was concentrated in vacuo and the residue was recrystalized from methanol to provide 2-bromo-1-(4-hydroxyphenyl)ethanone (1.73 g, 44% yield).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was recrystalized from methanol

Sources & evidence

ORD record
ord-1467451901b34110b095a0f9bc4d4385
Source dataset
uspto-grants-2006_08
Patent number
US07094896B2

Linked notes

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