Water → HCID 52987784, compound

HRID 554236Notes

Reaction equation

HRID 554236 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:12]N1C(=O)CCC1=O.O>O1CCCC1>[Br:12][C:4]1[NH:3][C:2]([CH3:1])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylate

Product 1

HCID 52987784HCID 52987784, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-1H-pyrrole-3-carboxylate (1.53 g) in tetrahydrofuran (20 mL) was added N-bromosuccinimide (1.78 g) at −78° C., and the mixture was stirred at the same temperature for 30 min. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure at not more than 5° C. The residue washed with hexane to give the title compound as a colorless solid (yield 2.26 g, 97%).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure at not more than 5° C
  5. washThe residue washed with hexane

Sources & evidence

ORD record
ord-f6d2786147fc4c8f982534891b8b7708
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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