1,2-Dibromoethane → 5-(2-Bromoethoxy)-2H-1,3-benzodioxole

HRID 1582759Notes

Reaction equation

HRID 1582759 reaction equation
[OH-].[Na+].[CH2:3]1[O:7][C:6]2[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:5]=2[O:4]1.[Br:13][CH2:14][CH2:15]Br>O>[CH2:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([O:12][CH2:15][CH2:14][Br:13])=[CH:8][C:6]=2[O:7]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 68289Sesamol

Product 1

HCID 143859615-(2-Bromoethoxy)-2H-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium hydroxide 0.15 g was dissolved in water 6 ml, and Sesamol 0.50 g and 1,2-dibromoethane 0.37 ml were added thereto and heated under reflux for 12 hours. After cooling, water was added thereto, and the product was extracted with ethyl acetate and further washed with brine. The product was dried over magnesium sulfate anhydride and evaporated. The residue was purified by (NH) silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 0.30 g, 34% was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. extractionthe product was extracted with ethyl acetate
  5. washfurther washed with brine
  6. dry with materialThe product was dried over magnesium sulfate anhydride
  7. customevaporated
  8. customThe residue was purified by (NH) silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 0.30 g, 34%
  9. customwas obtained

Sources & evidence

ORD record
ord-58a2c44ef85f4922a2539f440ebd0274
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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