1,2-Dibromoethane → HCID 18789953, compound

HRID 1106858Notes

Reaction equation

HRID 1106858 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Br:13][CH2:14][CH2:15]Br.[OH-].[Na+]>C(O)C>[Br:13][CH2:14][CH2:15][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 18789953HCID 18789953, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(Imidazol-1-yl)phenol (5 g, 31.3 mmol), 1,2-dibromoethane (8.09 g, 93.9 mmol) and sodium hydroxide (1.25 g, 31.3 mmol) were refluxed in ethanol for 24 h. Thereafter, the solvent was evaporated and the residue was diluted with a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The extracted organic layer was washed twice with a saturated aqueous solution of sodium chloride and dried with magnesium sulfate, followed by evaporation of the solvent. The residue was purified by column chromatography on silica gel using, as an eluent, methylene chloride containing 30% ethyl acetate. The fractions containing the product were subjected to evaporation to yield the end compound 1-bromo-2-[4-(imidazol-1-yl)phenoxy]ethane (3.58 g) in a solid form.

Workup

  1. customThereafter, the solvent was evaporated
  2. additionthe residue was diluted with a saturated aqueous solution of sodium bicarbonate
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extracted organic layer was washed twice with a saturated aqueous solution of sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. customfollowed by evaporation of the solvent
  7. customThe residue was purified by column chromatography on silica gel using, as an eluent
  8. additionThe fractions containing the product
  9. customwere subjected to evaporation

Sources & evidence

ORD record
ord-4a3975abf662411eb84ebdb4f43383fe
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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