Hydrochloric Acid → 2-Bromo-2'-methylacetophenone

HRID 2252859Notes

Reaction equation

HRID 2252859 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].Cl.[Br:12]Br>C(O)(=O)C>[Br:12][CH2:9][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 113402-MethylacetophenoneHCID 24408Bromine

Product 1

HCID 124306762-Bromo-2'-methylacetophenoneYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2′-Methylacetophenone (25.0 g, 186 mMole) was dissolved in glacial acetic acid (250 ml) and concentrated HCl (250 uL) was added followed by a dropwise addition of bromine (9.6 ml, 186 mMole) over 15 minutes. The mixture was stirred 3 hours and then concentrated under reduced pressure. The residue was taken up in ethyl ether and washed-with saturated NaHCO3 solution. The ether layer was dried over Na2SO4, filtered, and concentrated to yield 38.0 g, (96%) of crude 2-bromo-2′-methylacetophenone which was used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dry with materialThe ether layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3a098cca225c49cbbdb8cc429253ea0a
Source dataset
uspto-grants-2008_01
Patent number
US07323484B2

Reaction notes

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