Thionyl Chloride → Methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate

HRID 1368818Notes

Reaction equation

HRID 1368818 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:15]([C:16](O)=[O:17])=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:15]([C:16]([Cl:3])=[O:17])=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 18517418Methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate

Product 1

HCID 18517408Methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoateYield 94.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

2 drops of dimethylformamide and 11.9 g (0.1 mol) of thionyl chloride were added to a solution of 6.0 g (0.021 mol) of methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate and 50 ml of dry toluene. The solution was heated under reflux for 4 hours. After removal of the solvent under reduced pressure, 6.2 g of methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate were obtained.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 4 hours
  3. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-dc418e1dc96e465493303c86af10793d
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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