HCID 20461933, compound → 2,5-Bis(difluoromethoxy)benzene-1-sulfonyl chloride

HRID 326032Notes

Reaction equation

HRID 326032 reaction equation
[S:1]([O-:4])(O)=[O:2].[Na+].N([O-])=O.[Na+].[ClH:10].[F:11][CH:12]([F:25])[O:13][C:14]1[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:17][C:15]=1N>Cl.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[F:11][CH:12]([F:25])[O:13][C:14]1[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:17][C:15]=1[S:1]([Cl:10])(=[O:4])=[O:2]

Participants

7

Reactant 3

HCID 20461933HCID 20461933, compoundHCID 23665763Sodium Bisulfite2×HCID 23668193Sodium Nitrite

Product 1

HCID 204619272,5-Bis(difluoromethoxy)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

While cooling at 0° C., 21 ml of a 40% solution of sodium hydrogen sulfite are added dropwise to a solution of 3.0 g of copper sulfate pentahydrate in 90 ml of 32% hydrochloric acid. To the resultant solution is then made the simultaneous dropwise addition of 21 ml of a 40% solution of sodium hydrogen sulfite and a diazonium salt solution which has been cooled to -10° C. and obtained by the dropwise addition, with cooling, of 6.9 g of sodium nitrite in 10 ml of water, to a suspension of 50 ml of water, 15 of 32% hydrochloric acid and 26.2 g of 2.5-bis(difluoromethoxy)aniline hydrochloride. During this addition the temperature of the reaction mixture rises to 25° C., accompanied by the simultaneous evolution of gas. The reaction mixture is stirred for 2 hours, whereupon a brown oil precipitates. The organic phase is separated and the aqueous phase is extracted with methylene chloride. The organic phases are combined and evaporated to dryness, affording, as crude product, 12.7 g of 2.5-bis(difluoromethoxy)-phenyl sulfonyl chloride in the form of a brown oil.

Workup

  1. customobtained by the dropwise addition
  2. additionDuring this addition the temperature of the reaction mixture
  3. customrises to 25° C.
  4. customprecipitates
  5. customThe organic phase is separated
  6. extractionthe aqueous phase is extracted with methylene chloride
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-cad5bec53a9c49a499e4ec7620d6160d
Source dataset
uspto-grants-1984_04
Patent number
US04444583

Reaction notes

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