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

HRID 982201Notes

Reaction equation

HRID 982201 reaction equation
S(Cl)(Cl)=O.S(Cl)(Cl)(=O)=O.P(Cl)(Cl)(Cl)(Cl)Cl.P(Cl)(Cl)([Cl:18])=O.[Cl:21][C:22]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:23]=1[C:24](O)=[O:25]>O1CCOCC1.CS(C)=O.CN(C=O)C>[Cl:21][C:22]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:23]=1[C:24]([Cl:18])=[O:25]

Participants

9

Reactant 5

HCID 24386Thionyl Chloride2×HCID 24648Sulfuryl chlorideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 7371712-Chloro-4,5-difluorobenzoic acid

Product 1

HCID 101982172-Chloro-4,5-difluorobenzoyl chloride

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

In the chlorination of the reaction formula (a), thionyl chloride, sulfuryl chloride, phosphorus pentachloride or phosphorus oxychloride may be used as the chlorinating agents. Among them, thionyl chloride is preferred. The chlorination may be conducted by reacting 2-chloro-4,5-difluorobenzoic acid with the chlorinating agent at a reaction temperature of from 50 ° to 80° C. in an aprotic polar solvent such as DMF, DMSO or dioxane, or without a solvent, followed by isolation by a usual method such as distillation to obtain 2-chloro-4,5-difluorobenzoyl chloride.

Workup

  1. customof from 50 ° to 80° C.
  2. distillationwithout a solvent, followed by isolation by a usual method such as distillation

Sources & evidence

ORD record
ord-91470b33749242ecbb88d7dd5e1b1cd5
Source dataset
uspto-grants-1991_02
Patent number
US04994610

Reaction notes

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