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

HRID 1072045Notes

Reaction equation

HRID 1072045 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:11]Br.C(=O)(O)[O-].[Na+]>CCOCC>[CH:5]1[C:4]([C:1]([CH2:2][Br:11])=[O:3])=[CH:9][CH:8]=[C:7]([OH:10])[CH:6]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Acetylphenol (20 g) in ether (200 mL) was treated with bromine (6.8 mL) and stirred at ambient temperature for 18 hours. The solution was poured into saturated sodium bicarbonate, stirred for 30 minutes and the organic layer separated. The organic portion was washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated to afford the title compound (30 g).

Workup

  1. stirringstirred for 30 minutes
  2. customthe organic layer separated
  3. washThe organic portion was washed with saturated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-abb2cabfaead42b9be189b61df221614
Source dataset
uspto-grants-2005_06
Patent number
US06908929B2

Reaction notes

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