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

HRID 727245Notes

Reaction equation

HRID 727245 reaction equation
C([Mg]Cl)(C)C.[CH2:6]([O:8][C:9](=[O:14])[CH2:10][C:11]([OH:13])=O)[CH3:7].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]C(Cl)=O)=[CH:18][CH:17]=1.Cl>O1CCCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:11](=[O:13])[CH2:10][C:9]([O:8][CH2:6][CH3:7])=[O:14])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 70615Monoethyl malonateHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 178418918HCID 178418918, compound

Product 1

HCID 18944022Ethyl 4-(4-bromophenyl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

1 l (2 mol) of a 2M solution of isopropylmagnesium chloride in tetrahydrofuran is added dropwise to a solution of 125 g (0.95 mol) of malonic acid monoethyl ester in 1 l of tetrahydrofuran at 0° C. and the mixture is stirred at 20° C. for 1 hour. 146 g (0.63 mol) of 4-bromophenylacetyl chloride are then added dropwise at 20° C., and the reaction mixture is stirred at this temperature for 2 hours and brought to pH=3 with 1N hydrochloric acid. It is stirred overnight, the phases are separated, the aqueous phase is washed with diethyl ether, the combined organic phases are washed with water and aqueous sodium bicarbonate solution, the solvent is distilled off, the residue is dissolved in methylene chloride, the solution is dried with sodium sulphate and filtered over silica gel using methylene chloride and the solvent is removed on a rotary evaporator.

Workup

  1. stirringthe reaction mixture is stirred at this temperature for 2 hours
  2. stirringIt is stirred overnight
  3. customthe phases are separated
  4. washthe aqueous phase is washed with diethyl ether
  5. washthe combined organic phases are washed with water and aqueous sodium bicarbonate solution
  6. distillationthe solvent is distilled off
  7. dissolutionthe residue is dissolved in methylene chloride
  8. dry with materialthe solution is dried with sodium sulphate
  9. filtrationfiltered over silica gel
  10. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-de48bb460ed047e9bc35305ef6302048
Source dataset
uspto-grants-1998_01
Patent number
US05712296

Reaction notes

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