Dichloromethane → 2-Bromopropiophenone

HRID 2367396Notes

Reaction equation

HRID 2367396 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+]>CCOC(C)=O>[Br:14][CH:5]([CH3:6])[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

6

Reactant 4

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

Product 1

HCID 164522-BromopropiophenoneYield 98.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a CH2Cl2 solution (5 mL) of propiophenone (4.93 g, 36.82 mmol), a CH2Cl2 solution (5 mL) of bromine (6.49 g, 40 mmol) was gradually added at 15° C., followed by 1 hour of stirring. To the resulting solution, 30 mL of saturated NaHCO3 solution and 40 mL of EtOAc 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 (MgSO4), and subjected to distillation under reduced pressure to remove the solvent. The title compound (7.7 g) was obtained as a yellow oil. LC-MS (ES) m/z=214 [M+H]+.

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 (MgSO4)
  4. distillationsubjected to distillation under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-45b06bed1b90498884763e16336d59d2
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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