Water → Methyl 4-bromo-3,5-diethoxybenzoate

HRID 1096979Notes

Reaction equation

HRID 1096979 reaction equation
[Br:1][C:2]1[C:11](O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:13].[C:14](=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH3:21].O.CN([CH:27]=[O:28])C>>[Br:1][C:2]1[C:3]([O:13][CH2:20][CH3:21])=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[O:28][CH2:27][CH3:14]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 118602Benzoic acid, 4-bromo-3,5-dihydroxy-, methyl ester

Product 1

HCID 57930905Methyl 4-bromo-3,5-diethoxybenzoate

Procedure

Methyl 4-bromo-3,5-dihydroxybenzoate (10 g) was dissolved in DMF (80 mL), and potassium carbonate (13.2 g) and ethyl iodide (7.6 mL) were added to it, and stirred overnight at room temperature. The reaction liquid was poured into water with cooling with ice, extracted with ethyl acetate, the organic layer was washed with water and saturated saline water, and dried with sodium sulfate. Sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=1/0 to 90/10) to obtain the title compound as a white solid.

Workup

  1. customThe reaction liquid
  2. temperaturewith cooling with ice
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated saline water
  5. dry with materialdried with sodium sulfate
  6. customSodium sulfate was removed through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=1/0 to 90/10)

Sources & evidence

ORD record
ord-22306a4369ce47689fc57640bbbf8d82
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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