Hydrochloric Acid → HCID 22261503, compound

HRID 1610696Notes

Reaction equation

HRID 1610696 reaction equation
[Mg].II.[CH3:4][C:5]1[CH:6]=[C:7](Br)[CH:8]=[CH:9][CH:10]=1.[F:12][C:13]([F:20])([CH:17]([F:19])[F:18])[C:14](O)=[O:15].Cl>C(OCC)C>[F:12][C:13]([F:20])([CH:17]([F:19])[F:18])[C:14]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:4])[CH:10]=1)=[O:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 115603-BromotolueneHCID 69789FlupropanateHCID 5462224Magnesium

Product 1

HCID 22261503HCID 22261503, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

While stirring a solution of magnesium (14.1 g, 579 mmol) and iodine (one crumb) in diethyl ether (100 ml), 3-methylbromobenzene (90.0 g, 526 mmol) in diethyl ether (200 ml) was dropwise added at room temperature. After completion of the dropwise addition, the mixture was stirred overnight at room temperature. The reaction solution was cooled to −78° C. and a solution of 2,2,3,3-tetrafluoropropionic acid (25.61 g, 175.4 mmol) in diethyl ether (100 ml) was dropwise added, and the mixture was heated under reflux for 4 hrs. To the reaction solution was dropwise added 1N hydrochloric acid under ice-cooling. The diethyl ether layer was separated, and the aqueous layer was extracted with diethyl ether. The recovered diethyl ether solution was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=15/1) to give the objective substance.

Workup

  1. additionwas dropwise added at room temperature
  2. additionAfter completion of the dropwise addition
  3. temperatureThe reaction solution was cooled to −78° C.
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 4 hrs
  6. temperaturecooling
  7. customThe diethyl ether layer was separated
  8. extractionthe aqueous layer was extracted with diethyl ether
  9. dry with materialThe recovered diethyl ether solution was dried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=15/1)
  12. customto give the objective substance

Sources & evidence

ORD record
ord-0e49f7d438af4c089e4f8edd728cf976
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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