تفاعل #172161

معادلة التفاعل

(adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid tert-butylammonium salt

water

triphenylsulfonium bromide

→

triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate

المردود 92.0%

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter the reaction
2. 2
   أخرىthe reaction solution was separated into an organic layer
3. 3
   غسيلThe organic layer was washed with water
4. 4
   workup.DISSOLUTIONThe thus-obtained concentrated solution was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether
5. 5
   أخرىrecrystallized

الإجراء التجريبي

Within a 1-L three-neck flask, 122 g (purity: 99%, 307 mmol, 1.0 eq) of the (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid tert-butylammonium salt obtained in Example 5-b was dissolved in 500 g of chloroform. To the resulting solution, 400 g of water and 110.5 g (322 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, 166 g of target triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate was obtained (yield: 92%, purity: 99%). No fluorine ion (F−) was detected from any liquid waste of this step. Further, 200 ppb of sodium ion (Na+) was detected from the triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate obtained in this step.

المصدر