Dichloromethane → 2-Bromopropiophenone

HRID 2217784Notes

Reaction equation

HRID 2217784 reaction equation
C(Cl)Cl.[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])[CH2:5][CH3:6].[Br:14]Br.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:8]1([C:4](=[O:7])[CH:5]([Br:14])[CH3:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 71481-Phenyl-1-propanoneHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 164522-Bromopropiophenone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride solution (5 mL) of 4.934 g (36.82 mmol) of propiophenone, a methylene chloride solution (5 mL) of 6.4873 g (1.1 equivalents) of bromine was gradually added at 15° C., followed by 1 hour of stirring. To the resulting solution, 30 mL of a saturated sodium hydrogen carbonate solution and 40 mL of ethyl acetate were added to conduct extraction. The organic layer was washed with 20 mL of a 20 wt % sodium thiosulfate aqueous solution and then with 20 mL of saturated brine, dried over anhydrous magnesium sulfate, and subjected to distillation under a reduced pressure to remove the solvent. 1-Phenyl-2-bromo-1-propanone was obtained as an yellow, oily substance (8.7633 g, crude yield: 92%).

Workup

  1. extractionextraction
  2. washThe organic layer was washed with 20 mL of a 20 wt % sodium thiosulfate aqueous solution
  3. dry with materialwith 20 mL of saturated brine, dried over anhydrous magnesium sulfate
  4. distillationsubjected to distillation under a reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-38d6264d1c5341fdb549348f28302787
Source dataset
uspto-grants-2008_08
Patent number
US07408084B2

Reaction notes

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