Dibromomethane → HCID 69652311, compound

HRID 967477Notes

Reaction equation

HRID 967477 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([OH:11])[C:8]([OH:12])=[C:7]([OH:13])[CH:6]=1)[CH3:2].[C:15](=O)([O-])[O-].[K+].[K+].BrCBr>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[C:9]([OH:11])[C:8]2[O:12][CH2:15][O:13][C:7]=2[CH:6]=1)=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 13250Ethyl gallate

Product 1

HCID 69652311HCID 69652311, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

5 g (25.2 mmol) of 3,4,5-Trihydroxy-benzoic acid ethyl ester was dissolved in 50 ml of DMF and treated at 0° C. with 13.95 g (101 mmol) of potassium carbonate and 4.39 g (25.2 mmol) of dibromomethane. The reaction solution was heated at 60° C. for 3 h. The solvent was removed under reduced pressure, the residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (3/1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe solution was washed three times with water
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with n-heptane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-77337a6720e24936b78c8cbd003e537a
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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