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

HRID 1515420Notes

Reaction equation

HRID 1515420 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-c9a7063c9c4b471d95f25068f57b2e40
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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