Hydrochloric Acid → 2,2,2,4'-Tetrafluoroacetophenone

HRID 1577591Notes

Reaction equation

HRID 1577591 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[Mg].[F:10][C:11]([F:16])([F:15])[C:12](O)=[O:13].Cl>CCOCC>[CH:4]1[C:5]([C:12]([C:11]([F:16])([F:15])[F:10])=[O:13])=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 99931-Bromo-4-fluorobenzeneHCID 5462224Magnesium

Product 1

HCID 695642,2,2,4'-Tetrafluoroacetophenone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a three-neck flask, 52.5 g of 4-fluoro-1-bromobenzene are charged with 60 ml ether, then 7.3 g magnesium turnings. The walls of the flask are rinsed with a few ml ether. Small crystals of iodine are added thereto and the mixture is heated to reflux until all the magnesium has reacted with the same. The mixture is left to revert to room temperature, then a solution of 11.4 g trifluoro acetic acid in 15 ml ether is very slowly added in about 20 minutes. The inner temperature is kept at about 20°-30° by external cooling. The mixture is kept aside at room temperature for 15 minutes and then heated to reflux for three hours. The mixture is thereafter kept in a cool place for 12 hours. The cooled mixture is poured on a mixture of crushed ice and chlorhydric acid. The etherous phase is separated. The aqueous phase is extracted twice with 100 ml ether.

Workup

  1. washThe walls of the flask are rinsed with a few ml ether
  2. additionSmall crystals of iodine are added
  3. temperaturethe mixture is heated
  4. temperatureto reflux until all the magnesium
  5. customhas reacted with the same
  6. waitThe mixture is left
  7. customto revert to room temperature
  8. customis kept at about 20°-30° by external cooling
  9. temperatureheated
  10. temperatureto reflux for three hours
  11. waitThe mixture is thereafter kept in a cool place for 12 hours
  12. customThe etherous phase is separated
  13. extractionThe aqueous phase is extracted twice with 100 ml ether

Sources & evidence

ORD record
ord-57fedfa3a8d3433b9695bd2d6a85a2d7
Source dataset
uspto-grants-1981_09
Patent number
US04288453

Reaction notes

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