Methanethiol → HCID 23133064, compound

HRID 1351064Notes

Reaction equation

HRID 1351064 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+].[CH3:31][SH:32]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[CH3:31][S:32][C:26]1[CH:25]=[CH:24][C:23]([S+:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]2[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 878MethanethiolHCID 14798Sodium HydroxideHCID 16213837(4-Fluorophenyl)(diphenyl)sulfanium trifluoromethanesulfonate

Product 1

HCID 23133064HCID 23133064, compoundYield 67.5%

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 methanethiol 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 again 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-methylthiophenyl 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 again
  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-6c7f08708c60473487b030394cf85bcf
Source dataset
uspto-grants-2007_05
Patent number
US07217492B2

Reaction notes

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