Hydrochloric Acid → HCID 19973115, compound

HRID 1451931Notes

Reaction equation

HRID 1451931 reaction equation
Br[C:2]([F:9])([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])=[O:13].C(OCC)(=O)C.Cl>O1CCCC1.[Zn].O>[Cl:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([OH:13])[C:2]([F:9])([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 202502,2',4'-TrichloroacetophenoneHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 19973115HCID 19973115, compoundYield 52.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In 20 ml of dried tetrahydrofuran was suspended 0.97 g of zinc. To the suspension was dropwise added 3.0 g of ethyl bromodifluoroacetate under reflux. Then, 10 ml of a solution of 2.2 g of 2,2',4'-trichloroacetophenone dissolved in dried tetrahydrofuran was dropwise added under reflux. The resulting mixture was refluxed for 10 minutes. The insolubles were removed by filtration. The solvent was removed by distillation under reduced pressure. To the residue obtained were added 20 ml of ethyl acetate and 20 ml of water. The resulting solution was adjusted to pH 1.0 with 6N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant: n-hexane/toluene=1/2) to obtain 1.8 g of oily ethyl 4-chloro-3-(2,4-dichlorophenyl)-2,2-difluoro-3-hydroxybutyrate.

Workup

  1. temperatureunder reflux
  2. additionwas dropwise added
  3. temperatureunder reflux
  4. temperatureThe resulting mixture was refluxed for 10 minutes
  5. customThe insolubles were removed by filtration
  6. customThe solvent was removed by distillation under reduced pressure
  7. customTo the residue obtained
  8. customThe organic layer was separated
  9. washwashed with a saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customThe residue thus obtained
  13. customwas purified by a column chromatography (eluant: n-hexane/toluene=1/2)

Sources & evidence

ORD record
ord-a9ad75be270c43a4b52db1a7b204c4dc
Source dataset
uspto-grants-1997_02
Patent number
US05605921

Reaction notes

Loading…