Sodium ethoxide → 2-Bromo-4,5-dichloro-1-(ethoxymethyl)-1H-imidazole

HRID 979510Notes

Reaction equation

HRID 979510 reaction equation
Cl[CH2:2][N:3]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]1[Br:10].[O-:11][CH2:12][CH3:13].[Na+]>C(O)C>[CH2:12]([O:11][CH2:2][N:3]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]1[Br:10])[CH3:13]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 13732415HCID 13732415, compound

Product 1

HCID 1843072-Bromo-4,5-dichloro-1-(ethoxymethyl)-1H-imidazoleYield 22.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.06 g of 1-chloromethyl-2-bromo-4,5-dichloroimidazole, 0.54 g of sodium ethoxide and 40 ml of ethanol was heated under reflux for 10 hours. The reaction mixture was then concentrated under reduced pressure to obtain an oily product. This product was purified by column chromatography on silica gel to obtain 0.25 g of 1-ethoxymethyl-2-bromo-4,5-dichloroimidazole.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customto obtain an oily product
  5. customThis product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-596c85d4922e48db8a9a0c9b38786b39
Source dataset
uspto-grants-1987_05
Patent number
US04668693

Reaction notes

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