Thionyl Chloride → 3-(Chlorosulfonyl)-5-fluorobenzoyl chloride

HRID 2423242Notes

Reaction equation

HRID 2423242 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([F:18])[CH:17]=1)[C:12](O)=[O:13])(=[O:8])=[O:7]>CN(C)C=O>[Cl:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([F:18])[CH:17]=1)[C:12]([Cl:3])=[O:13])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 37487043-(chlorosulfonyl)-5-fluorobenzoic acid

Product 1

HCID 577806583-(Chlorosulfonyl)-5-fluorobenzoyl chlorideYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
75 °C

Procedure

One drop of N,N-dimethylformamide was added to a thionyl chloride (2.03 g) suspension of 3-(chlorosulfonyl)-5-fluorobenzoic acid (1.36 g), followed by stirring at 75° C. for 1 hour. The solvent was evaporated, and this was azeotroped with toluene to obtain 3-(chlorosulfonyl)-5-fluorobenzoyl chloride (1.47 g).

Workup

  1. customThe solvent was evaporated
  2. customthis was azeotroped with toluene

Sources & evidence

ORD record
ord-07191da2f9714a3ca3e72711eca565c4
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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