HCID 11716550, compound → Benzene, (4,4-difluoro-3-butenyl)-

Typical Procedures for the Preparation of 1,1-Difluoro-1-alkenes (10) from Alkyl-substitued Difluoromethyl Sulfones (4): Under an argon atmosphere, into a Schlenk flask containing 1,1-difluoro-4-phenylbutyl phenyl sulfone (4g) (100 mg, 0.32 mmol) in THF (4 mL) at −20° C., was added dropwise via a syringe t-BuOK (224 mg, 2 mmol) in DMF (4 mL). The reaction mixture was stirred at −20° C.˜rt for 1 h, and the completion of the reaction was monitored by 19F NMR [δ −89.6 (d, J=46.6 Hz, 1F); −91.6 (dd, J=46.6 Hz, 24.8 Hz, 1F)]. The reaction was then quenched by adding aqueous NaCl solution (10 mL), followed by extraction with Et2O (15 mL×3). The combined organic phase was dried over anhydrous Na2SO4, filtered, and the solvent was removed. The crude product was purified by a flash chromatography to give 1,1-difluoro-4-phenyl-1-butene (10a) (46 mg, 85% yield) as a colorless liquid. The characterization data is consistent with that early reported.8h

1. customThe reaction was then quenched
2. additionby adding aqueous NaCl solution (10 mL)
3. extractionfollowed by extraction with Et2O (15 mL×3)
4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
5. filtrationfiltered
6. customthe solvent was removed
7. customThe crude product was purified by a flash chromatography

ORD record

ord-758ba27d859c499789a9ff5b002b13dc

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119232B2