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

HRID 353726Notes

Reaction equation

HRID 353726 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-dc037eeccda64a73b8c563cd45c75e1d
Source dataset
uspto-grants-2004_06
Patent number
US06756374B2

Reaction notes

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