Dichloromethane → 2-Chloro-5-(chlorosulfonyl)-4-fluorobenzoyl chloride

HRID 421776Notes

Reaction equation

HRID 421776 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([S:12]([Cl:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].[Cl:16]CCl.C(Cl)(=O)C(Cl)=O>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([S:12]([Cl:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 45719302-Chloro-5-chlorosulfonyl-4-fluorobenzoic acid

Product 1

HCID 866439242-Chloro-5-(chlorosulfonyl)-4-fluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-chloro-5-(chlorosulfonyl)-4-fluorobenzoic acid (1.092 g, 4.0 mmol) was added dichloromethane (10 mL), oxalyl chloride (2.8 mL) and one small drop of N,N-dimethylformamide. The mixture was stirred at room temperature overnight. The mixture was then concentrated to give 2-chloro-5-(chlorosulfonyl)-4-fluorobenzoyl chloride which was used without additional purification.

Workup

  1. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-a438c6254c65435b8427bb678c83889e
Source dataset
uspto-grants-2012_01
Patent number
US08101614B2

Reaction notes

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