Sodium Carbonate → HCID 58244111, compound

HRID 389109Notes

Reaction equation

HRID 389109 reaction equation
Br[C:2]1[CH:16]=[C:15]([F:17])[C:5]([O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([F:18])[CH:3]=1.[C:19](=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.CB1OB(C)OB(C)O1>[F:17][C:15]1[CH:16]=[C:2]([CH3:19])[CH:3]=[C:4]([F:18])[C:5]=1[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 58243500HCID 58243500, compound

Product 1

HCID 58244111HCID 58244111, compoundYield 71.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 574072TrimethylboroxineSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-(4-bromo-2,6-difluorophenoxy)-2-methylpropanoate (200 mg), tetrakis-triphenylphosphine palladium (36 mg) and sodium carbonate (200 mg) were dissolved in a mixed solvent of dioxane (4.0 ml) and water (1.0 ml), trimethylboroxine (0.26 ml) was added thereto, followed by stirring under an argon atmosphere at 100° C. overnight. After cooling to room temperature, an insoluble substance was removed by celite filtration and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to obtain, as a colorless oily product, ethyl 2-(2,6-difluoro-4-methylphenoxy)-2-methylpropanoate (115 mg).

Workup

  1. additionwas added
  2. temperatureAfter cooling to room temperature
  3. customan insoluble substance was removed by celite filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-21ea2f0393314d7a8d1a2dbe8fbd52e2
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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