1-(Trifluoroacetyl)imidazole → 1-[4-Bromo-3-(trifluoromethyl)phenyl]-4,4,4-trifluoro-1,3-butanedione

Temperature

0 °C

To a solution of 1-[4-bromo-3-(trifluoromethyl)phenyl]-1-ethanone (1.34 g, 5.65 mmol) in THF (30 ml) was added lithium bis(trimethylsilyl)amide (1.0 M THF solution, 6.8 ml, 6.8 mmol) at −78° C. The mixture was stirred at 0° C. for 15 minutes and the solution was again cooled to −78° C. N-trifluoroacetylimidazole (1.15 g, 6.78 mmol) was added to the solution at the same temperature. The resulting mixture was stirred at −78° C. for 15 minutes and at room temperature for 2.5 hours. The reaction was quenched with 2N HCl (100 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 ml×2). The combined organic layer was washed with brine (200 ml), dried over MgSO4, and concentrated in vacuo to give 1.80 g (88%) of the title compound as a pale yellow solid.

1. temperaturethe solution was again cooled to −78° C
2. stirringThe resulting mixture was stirred at −78° C. for 15 minutes and at room temperature for 2.5 hours
3. customThe reaction was quenched with 2N HCl (100 ml)
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with ethyl acetate (100 ml×2)
6. washThe combined organic layer was washed with brine (200 ml)
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo

ORD record

ord-ca68389d6ab54a068f87c43c238c72d8

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06603008B1