Chlorosulfonic acid → 4-(2,2-Dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrobenzenesulfonyl chloride

HRID 838912Notes

Reaction equation

HRID 838912 reaction equation
[Cl:1][CH:2]([Cl:17])[C:3]([F:16])([F:15])[O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13].[Cl:18][S:19](O)(=[O:21])=[O:20]>>[Cl:17][CH:2]([Cl:1])[C:3]([F:15])([F:16])[O:4][C:5]1[C:6]([N+:12]([O-:14])=[O:13])=[CH:7][C:8]([S:19]([Cl:18])(=[O:21])=[O:20])=[C:9]([CH3:11])[CH:10]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 203252622-(2,2-Dichloro-1,1-difluoroethoxy)-4-methyl-1-nitrobenzene

Product 1

HCID 203252614-(2,2-Dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrobenzenesulfonyl chloride

Procedure

In a 500 ml stirred reaction flask equipped with thermometer, air condenser, dropping funnel and ice water bath was placed 50 ml of chlorosulfonic acid, and, while stirring at 0° to 10° C, there was added dropwise over a one-half hour period 17.2 g of 2-(2,2-dichloro-1,1-difluoroethoxy)-4-methyl-1-nitrobenzene. After stirring for 50 hours, the reaction mixture was poured over crushed ice. The organic phase was extracted with methylene chloride, and the extract was washed with dilute bicarbonate, decolorized with charcoal and dried. Evaporation of the solvent affored 10 g of 4-(2,2-dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrobenzenesulfonyl chloride as a solid melting at 60°-61° C.

Workup

  1. customreaction flask
  2. customequipped with thermometer, air condenser
  3. stirringwhile stirring at 0° to 10° C
  4. stirringAfter stirring for 50 hours
  5. additionthe reaction mixture was poured
  6. customover crushed ice
  7. extractionThe organic phase was extracted with methylene chloride
  8. washthe extract was washed with dilute bicarbonate
  9. customdried
  10. customEvaporation of the solvent affored 10 g of 4-(2,2-dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrobenzenesulfonyl chloride as a solid melting at 60°-61° C.

Sources & evidence

ORD record
ord-db0903df30ad49ebae83244e5c32ca66
Source dataset
uspto-grants-1978_06
Patent number
US04093644

Reaction notes

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