Oxalyl chloride → 3-(Chlorosulfonyl)-4-fluorobenzoyl chloride

HRID 873621Notes

Reaction equation

HRID 873621 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[F:14])[C:8](O)=[O:9])(=[O:4])=[O:3].C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[F:14])[C:8]([Cl:18])=[O:9])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 39298913-(Chlorosulfonyl)-4-fluorobenzoic acid

Product 1

HCID 581074393-(Chlorosulfonyl)-4-fluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-chlorosulfonyl-4-fluoro benzoic acid (2.5 g, 10 mmol) in methylene chloride at 0° C. is added oxalyl chloride (1.33 g, 11 mmol), followed by the addition of 1 drop of N,N,-dimethylformamide. The reaction mixture is warmed up to room temperature and stirred for an additional 4 h. The solvent is removed, and the residue is dried under vacuum for 1 hr to obtain the title compound as an oil, which is used for the next step without further purification.

Workup

  1. customThe solvent is removed
  2. customthe residue is dried under vacuum for 1 hr

Sources & evidence

ORD record
ord-104a5fa5897c4e989eb2bd193a57276c
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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