Water → Triphenylsulfonium ((1-adamantyl)methoxycarbonyl)difluoromethanesulfonate

HRID 84976

Reaction equation

HRID 84976 reaction equation
C([NH+](CC)CC)C.[C:8]12([CH2:18][O:19][C:20]([C:22]([F:28])([F:27])[S:23]([O-:26])(=[O:25])=[O:24])=[O:21])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.O.[Br-].[C:31]1([S+:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)(Cl)Cl>[C:8]12([CH2:18][O:19][C:20]([C:22]([F:28])([F:27])[S:23]([O-:26])(=[O:24])=[O:25])=[O:21])[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2.[C:44]1([S+:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11984010Triphenylsulfonium BromideHCID 131731910(Adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid triethylammonium salt

Product 1

HCID 44224732Triphenylsulfonium ((1-adamantyl)methoxycarbonyl)difluoromethanesulfonateYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Within a 1-L three-neck flask, 100 g (purity: 93%, 219 mmol, 1.0 eq) of the (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid triethylammonium salt obtained in Example 1-c was dissolved in 300 g of chloroform. To the resulting solution, 250 g of water and 78.9 g (223 mmol, 1.05 eq) of triphenylsulfonium bromide were added. This reaction solution was stirred for 1 hour. After the reaction, the reaction solution was separated into an organic layer and an aqueous layer. The organic layer was washed with water, followed by distillating chloroform from the washed organic layer. The thus-obtained concentrated solution was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether and then recrystallized. With this, 119 g of target triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate was obtained (yield: 92%, purity: 99%).

Workup

  1. customAfter the reaction
  2. customthe reaction solution was separated into an organic layer
  3. washThe organic layer was washed with water
  4. dissolutionThe thus-obtained concentrated solution was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether
  5. customrecrystallized

Sources & evidence

ORD record
ord-d6bb2c220ef44b70a03283ff2acd87a6
Source dataset
uspto-grants-2014_09
Patent number
US08846966B2

Linked notes

Loading…