Bromine → 2-Bromo-1-(4-propoxyphenyl)ethan-1-one

HRID 482625Notes

Reaction equation

HRID 482625 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1)[CH2:2][CH3:3].[Br:14]Br>C(OCC)C>[Br:14][CH2:12][C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[CH:10][CH:9]=1)=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 2601321-(4-Propoxyphenyl)ethan-1-one

Product 1

HCID 146173262-Bromo-1-(4-propoxyphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 133 g (750 mmole) of 4'-propoxyacetophenone dissolved in 500 ml of diethyl ether and heated to reflux was dropwise added 120 g (750 mmole) of bromine at a rate to maintain reflux and yet allow decolorization of the red color. The resulting organic solution was twice washed with 500 ml of water, washed once with 200 ml of brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. This mixture, upon analysis via gas chromatography was approximately 10% unbrominated starting material, 80% the desired monobrominated product, and 10% dibrominated compound. It was used as is in the next reaction. It could be crystallized from diethyl ether and hexane to yield pure monobrominated compound, a solid, mp 36°-38° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureto maintain
  4. temperaturereflux
  5. washThe resulting organic solution was twice washed with 500 ml of water
  6. washwashed once with 200 ml of brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customas is in the next reaction
  10. customIt could be crystallized from diethyl ether and hexane
  11. customto yield pure monobrominated compound

Sources & evidence

ORD record
ord-47214c48dbdf44f0869b79dbe07bd76a
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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