Potassium Iodide → HCID 86687891, compound

HRID 868931Notes

Reaction equation

HRID 868931 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:12]=[O:13])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26]Br>CN(C=O)C>[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[C:9]1[CH:12]=[O:13]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 178519948HCID 178519948, compound

Product 1

HCID 86687891HCID 86687891, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-phenyl-1H-imidazole-2-carbaldehyde (1.79 g, 10.4 mmol), potassium carbonate (2.87 g, 20.8 mmol), potassium iodide (2.94 g, 17.7 mmol) and 1,4-dibromobutane (4.49 g, 20.8 mmol) in dry DMF (35 mL) were heated to 50° C. and stirred for 4 hours. The mixture was poured into ice-water (100 mL), and washed with EtOAc (2×80 mL). The combined organic layers were washed with brine (2×100 mL). The organic layer was dried over sodium sulfate, filtered, concentrated and then purified by column chromatography to give 1-(4-bromobutyl)-4-phenyl-1H-imidazole-2-carbaldehyde as a colorless oil (2.1 g). MS (ESI): m/z 308 (M+H)+.

Workup

  1. washwashed with EtOAc (2×80 mL)
  2. washThe combined organic layers were washed with brine (2×100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-47d923c932704e8586bcf2fdc35d58df
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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