Cesium carbonate → HCID 53772666, compound

HRID 610448Notes

Reaction equation

HRID 610448 reaction equation
C(=O)([O-])[O-:2].[Cs+].[Cs+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29])=[CH:23][CH:22]=1>O.CN(C=O)C>[OH:2][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29])=[CH:23][CH:22]=2)=[O:17])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 45190564-(Bromomethyl)phenylacetic acidHCID 19601380HCID 19601380, compound

Product 1

HCID 53772666HCID 53772666, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of caesium carbonate (1.63 g, 5.00 mmol) in water (50 ml) was added 4-bromomethylphenylacetic acid (12) (1.15 g, 5.00 mmol), and the mixture was refluxed for one hour. After cooling, the reaction mixture was concentrated to dryness under reduced pressure. The residue obtained was suspended in DMF (10 ml). Thereto was added 2,2,2-trichloroethyl 4-bromomethylphenylacetate (13) (1.80 g, 5.00 mmol), and the resulting mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an oil which was purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=15:1) to give 2,2,2-trichloroethyl 4-(4-hydroxymethylphenylacetoxymethyl)phenylacetate (14) as a white solid (994 mg, yield 45%).

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  4. customThe residue obtained
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customto give an oil which
  10. customwas purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-cb3ea21db17845c180ff1e3ae24c0880
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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