2-Bromopropane → HCID 86654668, compound

HRID 880449Notes

Reaction equation

HRID 880449 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH:9]=[O:10])[NH:7][CH:8]=1.Br[CH:12]([CH3:14])[CH3:13]>CN(C)C=O>[I:3][C:4]1[CH:5]=[C:6]([CH:9]=[O:10])[N:7]([CH:12]([CH3:14])[CH3:13])[CH:8]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 46719534-iodo-1H-pyrrole-2-carbaldehyde

Product 1

HCID 86654668HCID 86654668, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (860 mg, 55% in mineral oil, 19.7 mmol) was added to a solution of 4-iodo-pyrrole-2-carbaldehyde (3.0 g, 13.2 mmol) in dry dimethylformamide at ambient temperature under a nitrogen atmosphere. After stirring for 15 min 2-bromopropane (3.87 mL, 40.9 mmol) was added and the reaction mixture heated at reflux for 16 h. The mixture was allowed to cool to ambient temperature, quenched with water and extracted with diethyl ether. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a crude residue. Purification by column chromatography over silica gel (60-120 mesh) using 2% ethyl acetate in petroleum ether afforded 4-iodo-1-isopropyl-pyrrole-2-carbaldehyde (1.5 g, 43%) as a brown liquid.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 16 h
  4. customquenched with water
  5. extractionextracted with diethyl ether
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a crude residue
  10. customPurification by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-f4514892561e4adb88c0b1fde885f87c
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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