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

HRID 443205Notes

Reaction equation

HRID 443205 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.CN(C)C=O>[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

5

Reactant 2

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

Product 1

HCID 27336892,3,4,5-Tetrafluorobenzoyl chlorideYield 100.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

In a 500 ml round bottom flask equipped with a magnetic stirrer, a reflux condenser and an inert gas supply 97.05 g of 2,3,4,5-tetrafluorobenzoic acid (2, 500 mmol) were suspended under argon and with stirring in 100 ml of n-hexane and 0.5 ml of N,N-dimethyl formamide. To this suspension 44 ml of thionyl chloride (d=1.64, 600 mmol) were added at room temperature, and the mixture was heated to reflux for 15 hours. The light yellowish solution was evaporated in a rotary evaporator at 50° C. reducing the pressure first to 200 torr until distillation ceased, then to 30 torr holding this pressure for 3 minutes to yield 107.1 g of the crude acid chloride 2a as a pale yellow liquid, which was kept under argon and directly used for step 3).

Workup

  1. customIn a 500 ml round bottom flask equipped with a magnetic stirrer, a reflux condenser
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 15 hours
  4. customThe light yellowish solution was evaporated in a rotary evaporator at 50° C.
  5. distillationuntil distillation
  6. customfor 3 minutes

Sources & evidence

ORD record
ord-2f69e571c1884d8f8f4d5afc49b6f4ce
Source dataset
uspto-grants-1999_04
Patent number
US05892040

Reaction notes

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