1,2-Dibromoethane → HCID 53689643, compound

HRID 744795Notes

Reaction equation

HRID 744795 reaction equation
Br[CH2:2][CH2:3]Br.[CH2:5]([O:7][C:8](=[O:18])[C:9]1[CH:17]=[C:15]([OH:16])[C:13]([OH:14])=[C:11]([OH:12])[CH:10]=1)[CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:5]([O:7][C:8]([C:9]1[CH:10]=[C:11]([OH:12])[C:13]2[O:14][CH2:3][CH2:2][O:16][C:15]=2[CH:17]=1)=[O:18])[CH3:6]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 13250Ethyl gallate

Product 1

HCID 53689643HCID 53689643, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 0.2 ml of 1,2-dibromoethane in 4 ml of dimethylformamide is added dropwise, four times at 2 hour intervals, to a solution, stirred at 100° C., of 2 g of gallic acid ethyl ester and 6.5 g of caesium carbonate in 80 ml of dimethylformamide. After being stirred for a further 2 hours at 100° C. the reaction mixture is concentrated by evaporation and the residue is partitioned between diethyl ether and water. The organic phases are dried over sodium sulfate and concentrated by evaporation. The title compound is obtained from the residue by FC (50 g of silica gel, methylene chloride-methanol=8:2): Rf (methylene chloride/methanol=8:2)=0.39.

Workup

  1. concentrationis concentrated by evaporation
  2. customthe residue is partitioned between diethyl ether and water
  3. dry with materialThe organic phases are dried over sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-321563f00e9e4633a4aeedebf7cff57e
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

Loading…