1,2-Dibromoethane → HCID 18693373, compound

HRID 660296Notes

Reaction equation

HRID 660296 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[O:1]1[CH2:17][CH2:16][O:8][C:7]2[CH:6]=[CH:5][C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][C:2]1=2

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 15132249Ethyl 2-(3,4-dihydroxyphenyl)acetate

Product 1

HCID 18693373HCID 18693373, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Ethyl 2-(3,4-dihydroxyphenyl)acetate (1.11 g, 5.66 mmol) and 1,2-dibromoethane (1.07 g, 5.69 mmol) in DMF (5 mL) was added cesium carbonate (3.71 g, 11.4 mmol). The reaction mixture was stirred for 2 hrs at 80° C. then cooled to room temperature. The mixture was diluted with H2O and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:4˜1:2) as eluant.

Workup

  1. temperaturethen cooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f374659878e343e594a71eedb9bb2d51
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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