Diphenyl sulfoxide → Diphenyl-4-methoxymethoxyphenylsulfonium trifluoromethanesulfonate salt

HRID 2061300Notes

Reaction equation

HRID 2061300 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]1([S:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)=O.CC(C)=O.[F:32][C:33]([F:46])([F:45])[S:34]([O:37]S(C(F)(F)F)(=O)=O)(=[O:36])=[O:35]>>[F:32][C:33]([F:46])([F:45])[S:34]([O-:37])(=[O:36])=[O:35].[C:19]1([S+:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 13679Diphenyl sulfoxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 10060101MethoxymethoxybenzeneHCID 18522661Acetone cardice

Product 1

HCID 49765819Diphenyl-4-methoxymethoxyphenylsulfonium trifluoromethanesulfonate saltYield 58.5%

Conditions

Temperature
0 °C

Procedure

About 100 g of the methoxymethoxybenzene manufactured in the synthesis example 1 and about 133.1 g of phenyl sulfoxide were mixed and stirred in about 1,200 ml of an MC, and then a temperature was reduced to about −78° C. using a dry ice-aceton. Next, about 240 g of trifluoromethanesulfonic anhydride was gradually dropped and stirred for about three hours using a dropping funnel at about −78° C. to perform a synthesis reaction (See Equation 2 below). Next, the synthesis reaction was terminated when an initiator on a thin layer chromatography (TLC) disappeared. Next, about 200 g of calcium carbonate was dissolved in about 1.5 L of water, and the reaction mixed liquid was added in a solvent cooled to about 0° C. and strongly stirred for about 20 minutes. Next, an organic phase was extracted, and further stirred in a calcium carbonate aqueous solution. Next, the extracted organic phase was washed using brine, and dried using magnesium sulphate. Next, the organic was filtered and concentrated to obtain about 200 g (a yield: about 58.5%) of a diphenyl-4-methoxymethoxyphenylsulfonium trifluoromethanesulfonate salt, and a structure of the diphenyl-4-methoxymethoxyphenylsulfonium trifluoromethanesulfonate salt was observed by 1H-NMR (See FIG. 2):

Workup

  1. additionwere mixed
  2. customwas reduced to about −78° C.
  3. stirringstirred for about three hours
  4. customat about −78° C.
  5. customa synthesis reaction (
  6. customNext, the synthesis reaction
  7. customwas terminated when an initiator on a thin layer chromatography (TLC)
  8. dissolutionNext, about 200 g of calcium carbonate was dissolved in about 1.5 L of water
  9. additionthe reaction mixed liquid
  10. additionwas added in a solvent
  11. stirringstrongly stirred for about 20 minutes
  12. extractionNext, an organic phase was extracted
  13. stirringfurther stirred in a calcium carbonate aqueous solution
  14. washNext, the extracted organic phase was washed
  15. customdried
  16. filtrationNext, the organic was filtered
  17. concentrationconcentrated

Sources & evidence

ORD record
ord-ea960b63320d4c968271fa36a0a80d7b
Source dataset
uspto-grants-2012_10
Patent number
US08283102B2

Reaction notes

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