Sodium Hydroxide → HCID 46186305, compound

Temperature

0 °C

The title compound, triphenylsulfonium (1-pyrrolidonemethoxycarbonyl)-difluoromethanesulfonate was prepared as depicted in Scheme 1 above and as follows: Sodium hydroxide (6.400 g, 160 mmol) was placed in a 100 mL round-bottom flask fitted with a condenser and water (30 mL) was added. The suspension was stirred magnetically for 30 min, then cooled down to 0° C. with an ice-bath. Methyl-2,2-difluoro-2-(fluorosulfonyl)acetate (9.605 g, 50 mmol) was added dropwise over 15 min. When the addition was complete, the mixture was left stirring under reflux for 18 hours. After this time, the mixture was cooled down to room temperature, filtered on a Buchner funnel to remove salts and the filtrate was acidified to pH=2 with aqueous HCl. The water was then removed under reduced pressure at 55° C. to give a colorless oil of sodium carboxydifluoromethanesulfonate. The next step was carried out assuming 100% conversion. 13C NMR (125 MHz, D2O) δ 113.69 (t), 165.53; 19F NMR (282 MHz, D2O) δ −108.83

1. customfitted with a condenser
2. additionWhen the addition
3. waitthe mixture was left
4. stirringstirring
5. temperatureunder reflux for 18 hours
6. temperatureAfter this time, the mixture was cooled down to room temperature
7. filtrationfiltered on a Buchner funnel
8. customto remove salts
9. customThe water was then removed under reduced pressure at 55° C.

ORD record

ord-e198a86970c24a7fbd7a7a7284902ec6

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609891B2