Hydrogen Bromide → 2-Bromo-2'-methylacetophenone

HRID 1871463Notes

Reaction equation

HRID 1871463 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[BrH:11].Br.[NH+]1C=CC=CC=1.O>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH2:9][Br:11]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 113402-MethylacetophenoneHCID 21226041Pyridinium hydrobromide

Product 1

HCID 124306762-Bromo-2'-methylacetophenone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3.0 g of 2'-methylacetophenone in 60 ml of acetic acid was added successively 9.7 ml of 47% hydrobromic acid and 8.6 g of pyridinium hydrobromide perbromide, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and a saturated sodium carbonate solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure to give 5.4 g of the title compound as a colorless oily material.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materiala saturated sodium carbonate solution, and dried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a6b5334d8eae45c09b7a29589070e1c5
Source dataset
uspto-grants-2000_08
Patent number
US06103736

Reaction notes

Loading…