Ethyl bromoacetate → HCID 86654666, compound

HRID 880445Notes

Reaction equation

HRID 880445 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH:9]=[O:10])[NH:7][CH:8]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>O1CCCC1>[CH:9]([C:6]1[N:7]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=[C:4]([I:3])[CH:5]=1)=[O:10]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 46719534-iodo-1H-pyrrole-2-carbaldehyde

Product 1

HCID 86654666HCID 86654666, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.62 g, 60% w/w dispersion in mineral oil, 67.9 mmol) was added to a solution of 4-iodo-1H-pyrrole-2-carbaldehyde (5.0 g, 22.6 mmol) in tetrahydrofuran (30 mL) over 10 min. The reaction mixture was stirred for 15 min, then ethyl bromoacetate (7.56 g, 45.2 mmol) was added and the mixture stirred for 2 h at ambient temperature. The reaction was quenched with methanol and concentrated in vacuo. The crude compound was then extracted into ethyl acetate. The organic layer washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under in vacuo to afford the crude compound. Purification by column chromatography over silica gel (100-200 mesh) using 2% ethyl acetate in petroleum ether afforded ethyl 2-(2-formyl-4-iodo-pyrrol-1-yl)acetate (3.4 g, 49%).

Workup

  1. stirringthe mixture stirred for 2 h at ambient temperature
  2. customThe reaction was quenched with methanol
  3. concentrationconcentrated in vacuo
  4. extractionThe crude compound was then extracted into ethyl acetate
  5. washThe organic layer washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under in vacuo
  9. customto afford the crude compound
  10. customPurification by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-b2cc9420453d48d88ef0c003c5a2d5b3
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

Loading…