Ethanesulfonylchloride, 2-chloro- → HCID 58557782, compound

A solution of 3,3-difluoropyrrolidine hydrochloride (0.3 g, 2.1 mmol, Matrix) and DIEA (0.37 mL, 2.1 mmol) in MeCN (5 mL) was stirred at about 50° C. for about 30 min. The reaction was cooled to ambient temperature and concd under reduced pressure. The solid was dissolved in MeCN (2 mL) and a solution of 2-chloroethanesulfonyl chloride (0.22 mL, 2.1 mmol) in Et2O (3 mL) was added at about −78° C. and stirred for about 2 h. To the reaction mixture was added DIEA (0.6 mL, 3.4 mmol) and stirred for about 1 h. The reaction was warmed to ambient temperature and the solvent was removed under reduced pressure. The residue was partitioned between DCM (5 mL) and water (2×2 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concd under reduced pressure to give crude 3,3-difluoro-1-(vinylsulfonyl)pyrrolidine (0.11 g, 27%) which was used without further purification: LC/MS (Table 1, Method b) Rt=2.04 min; MS m/z: 198 (M+H)+.

1. stirringstirred for about 1 h
2. temperatureThe reaction was warmed to ambient temperature
3. customthe solvent was removed under reduced pressure
4. customThe residue was partitioned between DCM (5 mL) and water (2×2 mL)
5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
6. filtrationfiltered

ORD record

ord-d73f2fe6511d4b6e894d0a5e3fbdbc69

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2