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

HRID 424432Notes

Reaction equation

HRID 424432 reaction equation
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[CH3:34][C:35]([C:37]1[CH:38]=[CH:39][C:40]([OH:43])=[CH:41][CH:42]=1)=[O:36]>O1CCCC1>[Br:1][CH2:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)=[O:36]

Participants

4

Reactant 2

HCID 74694'-HydroxyacetophenoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (276 g, 734 mmol) was added to a suspension of 4-hydroxyacetophenone (100 g, 734 mmol) in tetrahydrofuran (1000 ml) at room temperature. After stirring for 3 hours, the resulting suspension was filtered, and the filtrate was concentrated under reduced pressure. The residue was washed with diisopropyl ether to afford 2-bromo-1-(4-hydroxyphenyl)-ethan-1-one (85 g, 54%) as white crystals.

Workup

  1. filtrationthe resulting suspension was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-aa8bf0811c8e4cb381d6ad9030932b1f
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

Loading…