1,2-Dibromoethane → HCID 68638944, compound

HRID 1855391Notes

Reaction equation

HRID 1855391 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][C:8](=[O:10])[CH3:9])=[N:4][N:3]=1.Br[CH2:12][CH2:13]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2([C:8](=[O:10])[CH3:9])[CH2:13][CH2:12]2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 129554321-(5-Methyl-1,3,4-oxadiazol-2-yl)propan-2-one

Product 1

HCID 68638944HCID 68638944, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(5-methyl-[1,3,4]oxadiazol-2-yl)-propan-2-one (312 mg, 2.2 mmol), 1,2-dibromo-ethane (0.25 mL, 2.85 mmol), and potassium carbonate (770 mg, 5.6 mmol) in acetone (5 mL) was stirred at 60° C. for 16 h. Insoluble material was filtered off and the filtrate was diluted with ethyl acetate (30 mL). The solution was washed with water and brine, dried over sodium sulfate, and evaporated under reduced pressure. The residual material was purified by chromatography on silica gel using heptane/0-100% ethyl acetate as eluent to afford the title compound (75 mg, 20%) as pale-yellow oil.

Workup

  1. filtrationInsoluble material was filtered off
  2. additionthe filtrate was diluted with ethyl acetate (30 mL)
  3. washThe solution was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residual material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4b1df279078a48d797f25a1ac7344e77
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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