Hydrochloric Acid → Ethyl 3-(4-bromophenyl)-3-oxopropanoate

HRID 1610666Notes

Reaction equation

HRID 1610666 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=[O:3].[C:11](=O)([O:15]CC)[O:12][CH2:13][CH3:14].[H-].[Na+].Cl>C(O)C>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][C:11]([O:12][CH2:13][CH3:14])=[O:15])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7466p-BromoacetophenoneHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 2757149Ethyl 3-(4-bromophenyl)-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-bromoacetophenone (80 g, 0.40 mol), ethanol (1 ml) and diethyl carbonate (350 ml) was added sodium hydride (32 g, 60% in oil) by small portions under ice-cooling and the mixture was stirred at room temperature for 4 hrs. The reaction solution was cooled to 0° C. and 6N hydrochloric acid (200 ml) was added. The mixture was extracted with ethyl acetate (200, 100 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1-5:1) to give the objective substance (108.9 g, quantitative) as an oil.

Workup

  1. temperaturecooling
  2. temperatureThe reaction solution was cooled to 0° C.
  3. extractionThe mixture was extracted with ethyl acetate (200, 100 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1-5:1)
  8. customto give the objective substance (108.9 g, quantitative) as an oil

Sources & evidence

ORD record
ord-73372ff27c03442eb3d2f95ac242d423
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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