N-bromobutanimide → Ethyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate

HRID 2233821Notes

Reaction equation

HRID 2233821 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)Cl>[Br:12][C:3]1[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:6][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 965981H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl ester2×

Product 1

HCID 58066105Ethyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Ethyl 5-methyl-1H-pyrrole-2-carboxylate (Intermediate 20, 12.3 g, 0.803 mmol) was dissolved in anhydrous DCM and cooled to −5° C. N-bromosuccinimide (14.23 g; 0.0803 mmol) was added and the reaction stirred for 10 min and then poured into ice-cold 2 N sodium hydroxide (500 ml). The brown solution was extracted with EtOAc (2×150 ml), the combined organic extracts were washed with water, brine and dried over Na2SO4, then concentrated in vacuo to give a brown solid which was dried under vacuum. (16.5 g).

Workup

  1. extractionThe brown solution was extracted with EtOAc (2×150 ml)
  2. washthe combined organic extracts were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a brown solid which
  6. customwas dried under vacuum

Sources & evidence

ORD record
ord-6031e18a25d6478999be192b1631674e
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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