Thionyl Chloride → 4-Chloro-2,5-difluorobenzoyl chloride

HRID 982549Notes

Reaction equation

HRID 982549 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([F:12])[CH:3]=1.S(Cl)([Cl:15])=O>O>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27332744-Chloro-2,5-difluorobenzoic acid

Product 1

HCID 27364984-Chloro-2,5-difluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

38.5 g 4-chloro-2,5-difluorobenzoic acid (0.2 mole) was placed in a 250 mL, 3-necked roundbottom flask equipped with a magnetic stirbar, a thermometer, and a water-cooled condenser. 238 g thionyl chloride was added in one lot. The mixture was stirred and heated on a water bath. At about 58°-60° C. the solid dissolved with evolution of gas and formation of foam. The mixture was stirred and maintained at 60° C. until all the solid dissolved - about 30 minutes. It was then heated in a boiling water bath to reflux and held there for 2 hours.

Workup

  1. customequipped with a magnetic stirbar
  2. temperatureheated on a water bath
  3. dissolutionAt about 58°-60° C. the solid dissolved with evolution of gas and formation of foam
  4. stirringThe mixture was stirred
  5. dissolutiondissolved - about 30 minutes
  6. temperatureIt was then heated in a boiling water bath
  7. temperatureto reflux

Sources & evidence

ORD record
ord-67fd2ab4e04f4e7fa74abddc288608d8
Source dataset
uspto-grants-1991_02
Patent number
US04996355

Reaction notes

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