2-Pyrrolidone → Ethyl 3-bromo-2-oxo-3-phenylpropanoate

HRID 414712Notes

Reaction equation

HRID 414712 reaction equation
C1CNC(=O)C1.[Br:7][Br-]Br.[O:10]=[C:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].N1CCCC1=O>O1CCCC1>[Br:7][CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11](=[O:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 120252-PyrrolidoneHCID 12292599Ethyl 2-oxo-3-phenylpropanoate

Product 1

HCID 11161566Ethyl 3-bromo-2-oxo-3-phenylpropanoateYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

39.3 g (0.08 mole) of pyrrolidone hydrotribromide (PHT) are introduced portionwise at approximately 10° C. into a solution of 13.9 g (0.072 mole) of ethyl 2-oxo-3-phenylpropanoate (described by E. L. Eliel et al. J. Org. Chem. 37, 505, 1972) in 250 ml of tetrahydrofuran (THF) and 6.1 g (0.072 mole) of 2-pyrrolidone. The temperature of the mixture is allowed to return to 20° C. and the mixture is then heated to 50° C. for 1 h. The mixture is cooled and then poured onto ice. The mixture is extracted with ether and the organic phase washed with water, dried with MgSO4, filtered and evaporated. 18 g of oil are obtained, which is used in the crude state for the next stage of the reaction.

Workup

  1. customto return to 20° C.
  2. temperatureThe mixture is cooled
  3. additionpoured onto ice
  4. extractionThe mixture is extracted with ether
  5. washthe organic phase washed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c2f1b16225c2407ba22aee3bb78ac1b7
Source dataset
uspto-grants-1988_12
Patent number
US04794120

Reaction notes

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