2-Pyrrolidone → Ethyl 4-(2-bromopropanoyl)benzoate

HRID 606579Notes

Reaction equation

HRID 606579 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].C1CNC(=O)C1.[Br:22][Br-]Br.N1CCCC1=O>C1COCC1>[CH2:12]([O:11][C:9](=[O:10])[C:8]1[CH:14]=[CH:15][C:5]([C:1](=[O:4])[CH:2]([Br:22])[CH3:3])=[CH:6][CH:7]=1)[CH3:13]

Participants

4

Reactant 2

HCID 120252-PyrrolidoneHCID 24727466Ethyl 4-propanoylbenzoate

Product 1

HCID 71424477Ethyl 4-(2-bromopropanoyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-propionylbenzoate (2.0 mmol), pyrrolidinone hydrotribromide (2.1 mmol) and 2-pyrrolidinone (2.2 mmol) were heated in THF (20 mL) at 50 C for 2.5 h. The mixture was cooled, filtered, concentrated under vacuum and the residual oil partitioned between H2O and MTBE. The aqueous layer was extracted with MTBE, and the combined organic layers were washed with saturated aqueous sodium metabisulfite solution, H2O, brine, dried over MgSO4 and the solvent removed under vacuum. The residue was purified by flash column chromatography (9:1 IHexane: MTBE) to afford ethyl-4(2′-bromopropionyl)benzoate as a clear oil.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customthe residual oil partitioned between H2O and MTBE
  5. extractionThe aqueous layer was extracted with MTBE
  6. washthe combined organic layers were washed with saturated aqueous sodium metabisulfite solution, H2O, brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed under vacuum
  9. customThe residue was purified by flash column chromatography (9:1 IHexane: MTBE)

Sources & evidence

ORD record
ord-9f111510cfe34fd8b557726ce23a9836
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

Loading…