Hydrochloric Acid → 2-Bromo-2'-methylacetophenone

HRID 1838630Notes

Reaction equation

HRID 1838630 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. washwashed with saturated NaHCO3 solution
  3. dry with materialThe ether layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-301454b2974041f5a85849a6540ff48e
Source dataset
uspto-grants-2004_01
Patent number
US06673927B2

Reaction notes

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