Water → Ethyl 3-(3,5-bis(trifluoromethyl)phenyl)-3-cyanopropanoate

Temperatur

10 °C

3,5-Bis(trifluoromethyl)-phenylacetonitrile (1.4 mL, 1.0 eq.) was dissolved in THF (20 mL). The reaction mixture was cooled to −78° C. where a solution of NaHMDS (35% in THF) (4.34 mL, 1.05 eq.) was added dropwise. The reaction mixture was allowed to warm to 10° C. and stirred for 15 min. Then it was cooled to −78° C. where ethyl bromoacetate (0.87 mL, 1.0 eq.) was added. The reaction mixture was then allowed to warm to room temperature where it was stirred for 16 h. Reaction mixture was poured into water (50 mL) and was extracted with EtOAc (3×20 mL) The combined organic layers were washed with brine solution (3×50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 3.5 g of crude product, which was purified by chromatography (4% ethyl acetate in hexane) to give 1.2 g of ethyl 3-(3,5-bis(trifluoromethyl)phenyl)-3-cyanopropanoate (Yield 44.94%).

1. additionwas added dropwise
2. additionwas added
3. temperatureto warm to room temperature where it
4. stirringwas stirred for 16 h
5. customReaction mixture
6. extractionwas extracted with EtOAc (3×20 mL) The combined organic layers
7. washwere washed with brine solution (3×50 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto afford 3.5 g of crude product, which
12. customwas purified by chromatography (4% ethyl acetate in hexane)

ORD-Eintrag

ord-c485d724b7794d2f8790792dabe66d63

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09428490B2