Hydrochloric Acid → HCID 86673241, compound

Temperature

-78 °C

Lithium diisopropylamide (Aldrich Chemical Company, 2M in tetrahydrofuran/ethylbenzene 10.18 mL, 20.36 mmol) was added to tetrahydrofuran (8 mL) at −78° C. A solution of 1-(3-bromo-4-fluorophenyl)ethanone (4.01 g, 18.47 mmol) in tetrahydrofuran (8 mL) was added dropwise to the mixture. When the addition was complete the mixture was stirred at −78° C. for 30 min. Then a solution of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanone (4.50 g, 18.52 mmol) in tetrahydrofuran (8 mL) was added dropwise to the mixture so the temperature of the reaction mixture did not exceed −60° C. After the addition was complete the mixture was stirred at −78° C. for 60 min. The mixture was allowed to warm to 0° C. and then poured into 1N hydrochloric acid (100 mL). The mixture was extracted with ethyl acetate (2×100 mL), and the combined extracts were dried and evaporated. Chromatography of the residue on silica gel (eluted with 1:4 ethyl acetate/hexanes) gave the title product as a white solid (3.32 g, 39% yield) melting at 134-135° C. (after crystallization from ethyl acetate/hexanes).

1. additionWhen the addition
2. customdid not exceed −60° C
3. additionAfter the addition
4. stirringwas stirred at −78° C. for 60 min
5. temperatureto warm to 0° C.
6. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
7. customthe combined extracts were dried
8. customevaporated

ORD record

ord-595b95443d3142d29f3b4d41b73c8e9d

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513431B2