Water → HCID 52987784, compound

HRID 2090617Notes

Reaction equation

HRID 2090617 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.C(OCC)C>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

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 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 and diethyl ether were added to extract the reaction mixture. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure at 5° C. or below. The residue was washed with hexane to give the title compound as a colorless solid (yield 2.26 g, 97%).

Workup

  1. extractionto extract the reaction mixture
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure at 5° C. or below
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-2435104a8c7c474e9e645764bde49cf0
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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