Reacción #172159

Ecuación de reacción

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

m-chlorobenzoic acid

→

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

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfinic acid tert-butylammonium salt was totally consumed
2. 2
   LavadoThe thus-obtained organic layer was washed with 200 g of 10% aqueous sodium sulfite solution
3. 3
   Lavadowashed with 500 g of saturated sodium hydrogencarbonate solution
4. 4
   Lavadowashed twice with 500 g of water
5. 5
   workup.DISTILLATIONAfter distillation of chloroform from the washed organic layer
6. 6
   workup.DISSOLUTIONthe solid residue was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether
7. 7
   Otrorecrystallized

Procedimiento

Within a 1-L three-neck flask, 165 g (purity 84%, 364 mmol, 1.0 eq) of the (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfinic acid tert-butylammonium salt obtained in Example 4-a was dissolved in 600 g of chloroform. To the resulting solution, 94 g (382 mmol, 1.05 eq) of 70% m-chlorobenzoic acid was slowly added at 0° C. This reaction solution was stirred for 1 hour at room temperature. After that, it was confirmed by 19F NMR of the reaction solution that: the (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfinic acid tert-butylammonium salt was totally consumed; and there was no bromodifluoroacetic acid adamantane-1-ylmethyl ester detected as a by-product. The thus-obtained organic layer was washed with 200 g of 10% aqueous sodium sulfite solution, washed with 500 g of saturated sodium hydrogencarbonate solution and washed twice with 500 g of water. After distillation of chloroform from the washed organic layer, the solid residue was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether and then recrystallized. With this, 130 g of target (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid tert-butylammonium salt was obtained. The purity of the target compound was 99%; and the yield of the target compound was 90%.

Fuente