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

HRID 2213892Notes

Reaction equation

HRID 2213892 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-dd4cca4b90764a3ba3286992eda25505
Source dataset
uspto-grants-2006_09
Patent number
US07105670B2

Reaction notes

Loading…