Thionyl Chloride → 2,3,4,5-Tetrafluorobenzoyl chloride

HRID 443211Notes

Reaction equation

HRID 443211 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>CCCCCC>[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2975492,3,4,5-Tetrafluorobenzoic acid

Product 1

HCID 27336892,3,4,5-Tetrafluorobenzoyl chlorideYield 98.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a 1000 ml three-neck flask with thermometer, reflux condenser, 50 ml dropping funnel, mechanical stirrer, bubble counter, exhaust pipe and oil bath 0.5 ml of dimethylformamide were added with stirring to a suspension of 97.05 g of 2,3,4,5-tetrafluorbenzoic acid (8; 0.5 mol) in 100 ml of n-hexane. In the course of 10 min. 44 ml of thionyl chloride (0.61 mol) were added, and the reaction mixture was heated for 17 hours at reflux temperature. After cooling to room temperature, the n-hexane was evaporated off at 55° C. and increasing vacuum for 30 min. (at the end 3 min. at 55° C./40 torr). 104.8 g of 2,3,4,5-tetrafluoro-benzoic acid chloride (9) were obtained as a yellow, clear liquid, which was directly used in the next step.

Workup

  1. temperatureIn a 1000 ml three-neck flask with thermometer, reflux condenser
  2. custombubble counter, exhaust pipe and oil bath 0.5 ml of dimethylformamide
  3. additionwere added
  4. customIn the course of 10 min
  5. temperaturethe reaction mixture was heated for 17 hours
  6. temperatureat reflux temperature
  7. customthe n-hexane was evaporated off at 55° C.
  8. temperatureincreasing vacuum for 30 min. (at the end 3 min. at 55° C./40 torr)

Sources & evidence

ORD record
ord-72db74bd53844767a043ffe5b9b766c6
Source dataset
uspto-grants-1999_04
Patent number
US05892040

Reaction notes

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