Sodium Hydroxide → HCID 21097647, compound

HRID 471336Notes

Reaction equation

HRID 471336 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].F[C:10]1[CH:15]=[CH:14][C:13]([S+:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.[OH-].[Na+].[CH:31]1([SH:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[CH:31]1([S:37][C:10]2[CH:15]=[CH:14][C:13]([S+:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15290CyclohexanethiolHCID 16213837(4-Fluorophenyl)(diphenyl)sulfanium trifluoromethanesulfonate

Product 1

HCID 21097647HCID 21097647, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

267 g of 4-fluorophenyldiphenylsulfonium trifluoromethanesulfonate was dissolved in 2,000 g of dichloromethane, and the atmosphere of the system was replaced with nitrogen. After the addition of 2,000 g of a 10 wt % sodium hydroxide aqueous solution, 58 g of tetra-n-butylammonium bromide, and 72.1 g of cyclohexanethiol to the solution, the mixture was stirred at room temperature for 30 minutes. The mixture was transferred to a separating funnel, and allowed to stand. The aqueous layer was then removed. After washing the organic layer with 3,000 ml of distilled water, the aqueous layer was removed. The resulting dichloromethane solution was dried over anhydrous magnesium sulfate, and filtered. After evaporating dichloromethane from the solution, the residual liquid was dried under reduced pressure to obtain 192 g of 4-cyclohexylthiophenyldiphenylsulfonium trifluoromethanesulfonate. 192 g of 4-cyclohexylthiophenyldiphenylsulfonium trifluoromethanesulfonate was dissolved in 3,000 ml of methanol in a reaction flask. After the addition of 180 g of a 30 wt % hydrogen peroxide solution and 105 g of sodium tungstate dihydrate to the solution, the mixture was stirred at room temperature for 30 minutes. The resulting methanol solution was concentrated under reduced pressure, and the residue was dissolved in 3,000 g of dichloromethane. The solution was transferred to a separating funnel, and allowed to stand. The aqueous layer was then removed. After washing the organic layer with 1,000 ml of distilled water, the aqueous layer was removed. The resulting dichloromethane solution was dried over anhydrous magnesium sulfate, and filtered. After evaporating dichloromethane from the solution, the residual liquid was dried under reduced pressure to obtain 145 g of 4-cyclohexylsulfonylphenyldiphenylsulfonium trifluoromethanesulfonate. 145 g of 4-cyclohexylsulfonylphenyldiphenylsulfonium trifluoromethanesulfonate was dissolved in 1,000 g of methanol. The solution was subjected to ion-exchange chromatography (ion-exchange resin: Sephadex QAE A-25 manufactured by Aldrich (600 g)), and the collected organic layer was evaporated under reduced pressure to obtain 89 g of the compound represented by the following formula (XX).

Workup

  1. customThe mixture was transferred to a separating funnel
  2. customThe aqueous layer was then removed
  3. washAfter washing the organic layer with 3,000 ml of distilled water
  4. customthe aqueous layer was removed
  5. dry with materialThe resulting dichloromethane solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customAfter evaporating dichloromethane from the solution
  8. customthe residual liquid was dried under reduced pressure

Sources & evidence

ORD record
ord-c56c8f863a5c49d4a8fc3761bded10b6
Source dataset
uspto-grants-2014_01
Patent number
US08632945B2

Reaction notes

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