4-Nitrobenzenesulfonyl chloride → 2,2-Difluoropropyl 4-nitrobenzenesulfonate

2,2-Difluoropropan-1-ol (383 mg, 3.99 mmol) was combined with THF (3 mL). The solution was stirred at room temperature as 4-nitrobenzene-1-sulfonyl chloride (931 mg, 4.20 mmol) was added followed by triethylamine (0.611 mL, 4.39 mmol). After about 28 hours, the reaction mixture was diluted with THF (2 mL) and 4-dimethylaminopyridine (23 mg, 0.188 mmol) was added. After 16 hours the reaction mixture was diluted with 12 mL MTBE and 5 mL water and stirred for 5 minutes before the layers were separated. The organic layer was extracted with 1 M HCl (3 mL), 5% sodium carbonate (3 mL), brine (3 mL), and then water (3 mL). The organic layer was diluted with another 10 mL MTBE and extracted three times with 1 M NaOH (5 mL) and then water (5 mL). The organic layer was dried over sodium sulfate, filtered, concentrated on a rotovap, and dried under vacuum to give 2,2-difluoropropyl 4-nitrobenzenesulfonate (526 mg) as a pale yellow solid.

1. additionwas added
2. additionwas added
3. customwere separated
4. extractionThe organic layer was extracted with 1 M HCl (3 mL), 5% sodium carbonate (3 mL), brine (3 mL)
5. additionThe organic layer was diluted with another 10 mL MTBE
6. extractionextracted three times with 1 M NaOH (5 mL)
7. dry with materialThe organic layer was dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated on a rotovap
10. customdried under vacuum

ORD record

ord-bd7163d036de4e70ab5986cbe9bab3b9

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268819B2