Bromine → 2-bromo-1-(4-methoxyphenyl)propan-1-one

HRID 1633563Notes

Reaction equation

HRID 1633563 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.[Br:13]Br>C(O)(=O)C.Br>[Br:13][CH:10]([CH3:11])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:12]

Participants

5

Reactant 2

HCID 24408BromineHCID 671444-Propanoylanisole

Product 1

HCID 2991022-bromo-1-(4-methoxyphenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 176Acetic AcidSolvent

Procedure

0.30 mol of 4′-methoxypropiophenone is dissolved in 230 ml of glacial acetic acid and mixed with 3 drops of 48% HBr solution. In the stirred mixture, 0.30 mol of bromine is now slowly added in drops while being cooled in an ice bath such that the temperature in the flask does not exceed 15° C. The ice bath is removed, and it is stirred for about another 45 minutes in a continuous nitrogen stream to remove the HBR that is produced in the reaction. Then, it is carefully poured onto 300 ml of ice water. The settled precipitate is suctioned off, washed with several portions of water to remove all bromine and dried in a desiccator overnight. The crude product is recrystallized from 96% ethanol.

Workup

  1. temperaturewhile being cooled in an ice bath such that the temperature in the flask
  2. customdoes not exceed 15° C
  3. customThe ice bath is removed
  4. customto remove the HBR that
  5. customis produced in the reaction
  6. washwashed with several portions of water
  7. customto remove all bromine
  8. customdried in a desiccator overnight
  9. customThe crude product is recrystallized from 96% ethanol

Sources & evidence

ORD record
ord-bd520294d582439bbdabb4577911db33
Source dataset
uspto-grants-2003_01
Patent number
US06503938B1

Reaction notes

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