N-bromobutanimide → methyl 5-bromo-1-methyl-1H-pyrrole-3-carboxylate

HRID 1967115Notes

Reaction equation

HRID 1967115 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:3]1.C1C(=O)N([Br:18])C(=O)C1>O1CCCC1>[Br:18][C:6]1[N:2]([CH3:1])[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22737888Methyl 1-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 58172921methyl 5-bromo-1-methyl-1H-pyrrole-3-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 1-methyl-1H-pyrrole-3-carboxylate (690 mg, 4.96 mmol) and NBS (883 mg, 4.96 mmol) in tetrahydrofuran (24.800 ml) was stirred at 25° C. for 1 h. The solution was then partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (10-50% EtOAc in hexanes) affording methyl 5-bromo-1-methyl-1H-pyrrole-3-carboxylate (950 mg, 3.92 mmol, 79% yield) as an orange solid: LCMS (ES) m/e 218, 220 (M, M+2)+.

Workup

  1. customThe solution was then partitioned between H2O-DCM
  2. washthe aqueous phase was washed several times with DCM
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified via column chromatography (10-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-03197a00662f46109ff98fce23334fc7
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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