Thionyl Chloride → 3-Chloro-2,4,5-trifluorobenzoyl chloride

HRID 129552Notes

Reaction equation

HRID 129552 reaction equation
[Cl:1]C1C(F)=C(C=C(Cl)C=1F)C(F)=O.ClC1C(F)=C(F)C(F)=C(C=1)C(F)=O.ClC1C(Cl)=C(Cl)C(Cl)=C(C=1)C(Cl)=O.[F-].[K+].FC1C=C(F)C(F)=CC=1C(O)=O.[Cl:54][C:55]1[C:56]([F:66])=[C:57]([CH:61]=[C:62]([F:65])[C:63]=1[F:64])[C:58](O)=[O:59].S(Cl)(Cl)=O>S1(CCCC1)(=O)=O>[Cl:54][C:55]1[C:56]([F:66])=[C:57]([CH:61]=[C:62]([F:65])[C:63]=1[F:64])[C:58]([Cl:1])=[O:59]

Participants

9

Reactant 7

HCID 24386Thionyl ChlorideHCID 5211702,4,5-Trifluorobenzoic acidHCID 522689Potassium FluorideHCID 27342693-Chloro-2,4,5-trifluorobenzoic AcidHCID 54637643,5-Dichloro-2,4-difluorobenzoyl fluorideHCID 54637972,3,4,5-Tetrachlorobenzoyl chlorideHCID 135650155-Chloro-2,3,4-trifluorobenzoyl fluoride

Product 1

HCID 27822453-Chloro-2,4,5-trifluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

The benzoyl halides (1) used as starting materials for this synthetic route are prepared as follows: 3,5-dichloro-2,4-difluorobenzoyl fluoride (boiling point 97° /20 mbar; nD20 =1.5148) and 5-chloro-2,3,4-trifluorobenzoyl fluoride (boiling point 68°-70° /20 mbar; nD20 = 1.4764) are obtained together by heating tetrachlorobenzoyl chloride with potassium fluoride in sulpholane at elevated temperatures: ##STR14## The chlorination of 2,4,5-trifluorobenzoic acid in chlorosulphonic acid leads to 3-chloro-2,4,5-trifluorobenzoic acid which is reacted as the crude product with thionyl chloride to give 3-chloro-2,4,5-trifluorobenzoyl chloride (boiling point 94°/18 mbar; nD20 =1.5164): ##STR15##

Workup

  1. customare prepared
  2. customnD20 = 1.4764) are obtained together

Sources & evidence

ORD record
ord-f50a509456c44e71849c0418d6c9891f
Source dataset
uspto-grants-1995_11
Patent number
US05468861

Reaction notes

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