(p-Hydroxyphenyl)diphenylsulfonium trifluoromethanesulfonate → Bicyclo[2.2.1]heptane-2-carboxylic acid-2,2-difluoro-2-sulfo-ethyl ester diphenyl-4-hydroxyphenylsulfonium salt

HRID 2061302Notes

Reaction equation

HRID 2061302 reaction equation
FC(F)(F)S([O-])(=O)=O.[C:9]1([S+:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na].[F:30][C:31]([F:47])([S:43]([OH:46])(=[O:45])=[O:44])[CH2:32][O:33][C:34]([CH:36]1[CH2:41][CH:40]2[CH2:42][CH:37]1[CH2:38][CH2:39]2)=[O:35]>O>[C:9]1([S+:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F:47][C:31]([F:30])([S:43]([OH:46])(=[O:45])=[O:44])[CH2:32][O:33][C:34]([CH:36]1[CH2:41][CH:40]2[CH2:42][CH:37]1[CH2:38][CH2:39]2)=[O:35]

Participants

4

Reactant 2

HCID 22389942(p-Hydroxyphenyl)diphenylsulfonium trifluoromethanesulfonateHCID 86642223Bicyclo[2.2.1]heptane-2-carboxylic acid-2,2-difluoro-2-sulfo-ethyl ester sodium salt

Product 1

HCID 86642222Bicyclo[2.2.1]heptane-2-carboxylic acid-2,2-difluoro-2-sulfo-ethyl ester diphenyl-4-hydroxyphenylsulfonium saltYield 71.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

About 10 g of the diphenyl-4-hydroxyphenylsulfonium trifluoromethanesulfonate salt manufactured in the synthesis example 3 and about 10 g of a bicyclo[2.2.1]heptane-2-carboxylic acid-2,2-difluoro-2-sulfo-ethyl ester sodium salt were dissolved in about 100 ml of MC and about 100 ml of water, and a synthesis reaction (see Equation 4 below) was performed while stirring for about three hours. In this instance, a process of the synthesis reaction was observed by 19F NMR using a small amount of an extracted organic phase. The organic phase was extracted when the synthesis reaction was terminated, a solvent was removed, and the organic phase was washed using an MC of a soluble solvent and hexane of a sparingly soluble solvent. Next, the solvents were removed, and drying under a reduced pressure was performed to obtain about 9.42 g of a bicyclo[2.2.1]heptane-2-carboxylic acid-2,2-difluoro-2-sulfo-ethyl ester diphenyl-4-hydroxyphenylsulfonium salt, and a structure of the bicyclo[2.2.1]heptane-2-carboxylic acid-2,2-difluoro-2-sulfo-ethyl ester diphenyl-4-hydroxyphenylsulfonium salt was observed by 1H-NMR:

Workup

  1. customa synthesis reaction (see Equation 4 below)
  2. customIn this instance, a process of the synthesis reaction
  3. extractionThe organic phase was extracted when
  4. customthe synthesis reaction
  5. customwas terminated
  6. customa solvent was removed
  7. washthe organic phase was washed
  8. customNext, the solvents were removed
  9. customdrying under a reduced pressure

Sources & evidence

ORD record
ord-eaa42cd126ac4753ae6b5dda63e30bab
Source dataset
uspto-grants-2012_10
Patent number
US08283102B2

Reaction notes

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