Sodium Hydroxide → HCID 21097647, compound

HRID 1351056Notes

Reaction equation

HRID 1351056 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 63.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

26.7 g of 4-fluorophenyl diphenylsulfonium trifluoromethanesulfonate was dissolved in 200 g of dichloromethane in a reaction flask, in which the atmosphere was replaced with nitrogen. 200 g of 10 wt % sodium hydroxide aqueous solution, 5.8 g of tetra-n-butylammonium bromide, and 6.71 g of cyclohexane thiol were added. The mixture was stirred for 30 minutes at room temperature and transferred to a separatory funnel, shaken, and allowed to stand still. The water layer was removed. After the addition of 300 ml of distilled water, the mixture was shaken and allowed to stand still. The water layer was removed. The resulting dichloromethane solution was dried using anhydrous magnesium sulfate and filtered. After evaporating dichloromethane from the dried solution, the residual liquid was dried under reduced pressure to obtain 19.2 g of 4-cyclohexylthiophenyl diphenylsulfonium trifluoromethane sulfonate.

Workup

  1. customtransferred to a separatory funnel
  2. stirringshaken
  3. customThe water layer was removed
  4. additionAfter the addition of 300 ml of distilled water
  5. stirringthe mixture was shaken
  6. customThe water layer was removed
  7. dry with materialThe resulting dichloromethane solution was dried
  8. filtrationfiltered
  9. customAfter evaporating dichloromethane from the dried solution
  10. customthe residual liquid was dried under reduced pressure

Sources & evidence

ORD record
ord-ea6c79ae070b47099cee46645e9e6c23
Source dataset
uspto-grants-2007_05
Patent number
US07217492B2

Reaction notes

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