Sulfuric Acid → 2',4',5'-Trifluoroacetophenone

HRID 1030091Notes

Reaction equation

HRID 1030091 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:13](OCC)C.S(=O)(=O)(O)O>C(O)C>[CH3:13][C:4]([C:3]1[C:2]([F:1])=[CH:10][C:9]([F:11])=[C:8]([F:12])[CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 1451642,4,5-Trifluorobenzoyl chloride

Product 1

HCID 5944172',4',5'-TrifluoroacetophenoneYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

194.5 g (1 mol) of 2,4,5-trifluorobenzoyl chloride were initially introduced into 100 ml of diethyl ether and heated to boiling under reflux. 1.1 mol of ethoxymagnesium malonic ester dissolved in 100 ml of ethanol and 125 ml of diethyl ether were then allowed to drop in in the course of 30 minutes and the mixture was stirred for 1 hour under reflux. After cooling, the reaction mixture was stirred into 500 ml of ice water and adjusted to a pH of 1 with concentrated sulphuric acid, and the organic material (345 g) was separated off. This organic material was dissolved in 300 ml of acetic acid and, after adding 37.5 ml of concentrated sulphuric acid, heated to reflux until evolution of CO2 had ended, which took 6 hours. The reaction mixture was then cooled and poured into water, and the organic phase was separated off and distilled. 83 g of product having a boiling point at 10 mbar of 63° to 64° C. were obtained. This corresponds to a yield of 47% of theory.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customto drop in in the course of 30 minutes
  4. temperatureunder reflux
  5. temperatureAfter cooling
  6. customthe organic material (345 g) was separated off
  7. dissolutionThis organic material was dissolved in 300 ml of acetic acid
  8. additionafter adding 37.5 ml of concentrated sulphuric acid
  9. temperatureheated
  10. temperatureto reflux until evolution of CO2
  11. waitwhich took 6 hours
  12. temperatureThe reaction mixture was then cooled
  13. additionpoured into water
  14. customthe organic phase was separated off
  15. distillationdistilled
  16. customat 10 mbar of 63° to 64° C.
  17. customwere obtained

Sources & evidence

ORD record
ord-9a94c4ac70b74055bd9a1bf8cbf3ebcc
Source dataset
uspto-grants-1992_04
Patent number
US05104879

Reaction notes

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