Ethyl Acetate → 3-(4-Bromoanilino)-3-oxopropanoic acid

HRID 522368Notes

Reaction equation

HRID 522368 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13]CC)=[O:12])=[CH:4][CH:3]=1.[OH-].[Na+].C(OCC)(=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:16])[CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 123249573-(4-Bromoanilino)-3-oxopropanoic acid ethyl ester

Product 1

HCID 37964503-(4-Bromoanilino)-3-oxopropanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1 (16.63 g) was dissolved in THF (150 mL) and 2N NaOH (145 mL) was added over 15 minutes. The reaction was stirred for 24 hours. The reaction mixture was concentrated to remove the THF. Diethyl ether (20 mL) was added and the layers were separated. The aqueous layer was acidified to pH=2.2 with 1N HCl which resulted in the precipitation of solids. Ethyl acetate was added until the solids were dissolved and the layers were separated. The organic extract was dried with sodium sulfate, filtered and concentrated to give 14.7 g of a cake.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the THF
  3. additionDiethyl ether (20 mL) was added
  4. customthe layers were separated
  5. customresulted in the precipitation of solids
  6. dissolutionwere dissolved
  7. customthe layers were separated
  8. extractionThe organic extract
  9. dry with materialwas dried with sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto give 14.7 g of a cake

Sources & evidence

ORD record
ord-df6b92635cf1422db4d2ce2c10a12b86
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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