Tetrahydrofuran → 2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-ethenylbenzonitrile

To a solution of NaH (0.798 g, 19.96 mmol) in dry THF (15 mL) was added methyltriphenylphosphonium bromide (7.13 g, 19.96 mmol). The mixture was stirred at room temperature for 0.5 h. Then 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-formylbenzonitrile (5.0 g, 15.35 mmol) was added. Stirring continued for 1.5 h, and the mixture was quenched by ice water. THF was removed by evaporation; the aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound (1.8 g, 5.56 mmol, 36.2% yield).

1. stirringStirring
2. waitcontinued for 1.5 h
3. customthe mixture was quenched by ice water
4. customTHF was removed by evaporation
5. extractionthe aqueous layer was extracted with DCM
6. washThe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD-Eintrag

ord-db6c85402d914284a45506163442fd60

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08637536B2